CN102702139A - Thermal extraction method and product - Google Patents
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- CN102702139A CN102702139A CN2012100964879A CN201210096487A CN102702139A CN 102702139 A CN102702139 A CN 102702139A CN 2012100964879 A CN2012100964879 A CN 2012100964879A CN 201210096487 A CN201210096487 A CN 201210096487A CN 102702139 A CN102702139 A CN 102702139A
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Abstract
The present invention is related to a thermal extract of a plant material and methods of extraction thereof. The method of producing a thermal extract from a plant starting material by means of a thermal extraction of the starting material wherein the improvement consists in requiring smaller amounts of costly and/or toxic organic solvents for the extraction and partitioning steps.
Description
Related application
The application is dividing an application of No. 200780020439.9 application for a patent for invention (the international application no PCT/CA2007/000535) being entitled as " thermal extraction method and product " that submit to China national Department of Intellectual Property on April 2nd, 2007.
Technical field
The present invention relates to extract the method for producing extract and extract product with heat through heat.
Background technology
The desired compound of extraction normally carries out through solvent extraction process from starting material.
Comprising that desired component is extracted in the use solvent extraction on many starting material of biomass now.An one of which representative instance is from biomass, to extract Taxan.
Taxan is one group of diterpene-kind compound, wherein has some to be proved to be for cancer and is useful such as the treatment of other grave illness of multiple sclerosis and ephrosis.Especially, confirmed that taxane compounds taxol, Docetaxel, Baccatine III, 10-O-deacetylation crust card fourth III (10-DAB or DAB), 13-ethanoyl-9-hydroxyl crust card fourth III (DHB), Taxol B and prostratin (12-deoxidation phorbol 13-acetic ester (12-deoxyphorbol 13-acetate)) are useful in medicinal application.For example, taxol is used to cancer therapy (being gone on the market with
by Bristol Myers Squibb) at present.Some Taxan; Such as taxol and Docetaxel; Can under having the situation of extra chemical modification, directly be used in the medicinal application, and other Taxan (for example DAB and DHB) is considered to produce the parent of other Taxan such as taxol and Docetaxel.
The main source of Taxan is bark, needle and the clipping (clipping) of Japanese yew (Chinese hemlock spruce) tree that belongs to Cercocarpus.Regrettably, even the concentration of Taxan in Japanese yew is higher than the concentration in other seeds, its absolute concentration also is low-down.For example; Be reported in the general sample, from the bark of yew tree, only obtained 0.01% taxol output, and the taxol output that from clipping and needle, obtains (people such as Huang in the scope of 0.003～0.015% (dry basis); J.Nat.Prod.; 49:665,1986), wherein first extraction is solvent extraction.In addition, rareness and growth phase cause reforesting and resource management can not be caught up with the reasonable worry of demand when slow yew tree relatively.Though designed the synthetic and semi-synthetic channel of producing taxol, they are too complicated and not economic usually for commercial prodn.The semisynthesis of producing Docetaxel also designs.
The commercial at present taxol and the working method of other Taxan are complicated and expensive.Its unit operation mainly is a physical method, comprising: harvesting/collection, grinding, covering, primary solvent extract and separate to obtain thick Taxan product.After producing thick Taxan product, in other solvent extraction and other purification step, can reclaim and purification of paclitaxel.In many cases, through chemical process other natural Japanese yew alkane is changed into the taxol or the Docetaxel of extra yield.
The method of from starting material, separating other compound at present also usually comprises the initial step of solvent extraction, and it has also removed desired compound when removing a large amount of impurity.Therefore, often carrying out one or more liquid allocation step to be concentrated in compound concentrations desired in the extracting solution, is several chromatographic steps in some cases subsequently.
A shortcoming of these methods is that they need a large amount of expensive and deleterious sometimes organic solvents with allocation step in order to extract.Commercial, this means and to pay very high fund and production cost for material, qualified technical skill, qualified technician and Infrastructure.
Therefore, need a kind of method of separating compound, this method can reduce or eliminate the demand of poisonous and expensive organic solvent in a large number.
Summary of the invention
According to a wide aspect of the present invention; Provide a kind of and extracted the method for producing heat extraction substrate through raw-material heat; Comprise: starting material are heated to certain temperature and for some time, and it enough extracts a certain amount of required compound and quite a large amount of required compounds and is not converted into one or more other compound from starting material.
According to a further aspect in the invention, provide a kind of and extracted the method that the extract of Taxan is rich in acquisition through heat.
In an illustrative embodiments of the present invention; Provide a kind of and extracted the method for from the biomass starting material that contain diterpene-kind compound, producing the heat extraction substrate that is rich in Taxan through the raw-material heat of biomass; Comprise: the biomass starting material are heated to certain temperature and for some time, and it enough extracts a certain amount of Taxan and quite a large amount of Taxans and is not converted into one or more other compound.
In an illustrative embodiments of the present invention, provide a kind of production to comprise the method for the heat extraction substrate of required compound, comprising: the starting material adding is comprised in the heat extraction system of closed container, thermal source and at least one retrieving arrangement; In this heat extraction system, starting material are heated to certain temperature and for some time, it is enough produced the product stream that contains a certain amount of required compound and quite a large amount of required compounds and is not converted into one or more other compound; In at least one device of at least one retrieving arrangement, from the product stream that is rich in required compound, collect at least one cut to obtain heat extraction substrate.
In a further illustrative embodiments of the present invention; A kind of method of from the biomass starting material that contain diterpene-kind compound, producing the heat extraction substrate that is rich in Taxan is provided, has comprised: the adding of biomass starting material has been comprised in the heat extraction system of closed container, thermal source and at least one retrieving arrangement; In this heat extraction system, the biomass starting material are heated to certain temperature and for some time, it is enough produced the product stream that contains a certain amount of Taxan and quite a large amount of Taxans and is not converted into one or more other compound; In at least one device of at least one retrieving arrangement, from product stream, collect at least one cut that contains Taxan to obtain to be rich in the heat extraction substrate of Taxan.
According to another illustrative embodiments of the present invention, a kind of extract that is rich in Taxan is provided.
According to another illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in terpenes or terpenoid that obtains through the inventive method is provided.
According to another further illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in Taxan that obtains through the inventive method is provided.
According to a further illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in flavonoids that obtains through the inventive method is provided.
According to another illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in l-Epicatechol that obtains through the inventive method is provided.
According to another illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in catechin that obtains through the inventive method is provided.
According to another illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in theine that obtains through the inventive method is provided.
According to also illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in Vanillin that obtains through the inventive method is provided.
According to another illustrative embodiments of the present invention, a kind of heat extraction substrate that is rich in β-Gu Zaichun that obtains through the inventive method is provided.
According to another further illustrative embodiments of the present invention; A kind of extract that contains taxol and 10-O-deacetylation crust card fourth III is provided; Wherein based on weight ratio, much about 10 times of the amounts of the 10-O-deacetylation crust card fourth III that in this extract, exists than the amount of taxol.
According to another further illustrative embodiments of the present invention; A kind of extract that contains taxol and 13-ethanoyl-9-hydroxyl crust card fourth III is provided; Wherein based on weight ratio, much about 10 times of the amounts of the 13-ethanoyl that in this extract, exists-9-hydroxyl crust card fourth III than the amount of taxol.
According to another further illustrative embodiments of the present invention, a kind of extract that contains taxol and 7-table-taxol is provided, wherein based on weight ratio, much about 10 times of the amounts of the 7-table-taxol that in this extract, exists than the amount of taxol.
Description of drawings
Fig. 1 is the synoptic diagram that extracts an instance of system according to the heat that is fit to of an embodiment of the invention.
Fig. 2 is the schema of diagram according to the inventive method of embodiment 1C.
Embodiment
It has been observed that hot extraction can be used as the alternate process for extracting of solvent extraction.
Heat is extracted and is meaned the initial step that does not need at present relevant with solvent extraction process raw material solvent extraction.
The term that uses in this article " heat is extracted " (it also can be called as " thermal distillation " perhaps " Rapid Thermal distillation ") refers to a kind of process for extracting, wherein uses heat to come from the starting material that are fit to, to isolate one or more required compounds.Through in enclosed environment, applying heat to suitable starting material, can one or more required compounds be disengaged, keep, reclaim also the not ruined state of maintenance basically with mode.Therefore hot extraction can be used for extracting naturally occurring required compound and not having chemical conversion from starting material, and said naturally occurring compound is found in starting material.Though hot extraction possibly destroy some compound in the starting material or chemical conversion, quite a large amount of required compounds is not degraded perhaps with other mode by chemically changed.Extract " the naturally occurring required compound " or " required compound " that obtain through heat and refer to the compound that is stored in the starting material, and this wherein quite a large amount of compounds is not another kind of compound with other mode by chemical transformation perhaps by thermal extraction method degraded of the present invention.
Can raw material used in this invention not special restriction, if it provide one or more required compounds the source and can be through the extraction of being heated.For example, biomass are the common raw materials that are used for solvent extraction process, and it also can be the suitable starting material that are used for the inventive method.For example, biomass can be plant-derived.Any cut of plant all possibly be applicable to the heat extraction, comprises bark, needle, stem, root, leaf, seed, the vegetable cell in cultivation etc.; Or its mixture.The biological material that comes from plant used in this invention can be, for example, just acquisition state, dried state or saturation state.
If one or more Taxans are required compounds, be considered to the source of fabulous Taxan so usually such as those biological materials that contain diterpene-kind compound that are derived from yew tree.For example, all or various ingredients of the kind that belongs to of Cercocarpus or Australia Ramulus et folium taxi cuspidatae (Austrotaxus) can be as the Taxan sources.
In another invention embodiment, hot extraction can be used for from the starting material that are fit to, extracting flavonoids.From various plants, characterized and surpassed 5,000 kinds of naturally occurring flavonoidss (comprising isoflavonoid compound and neoflavonoid compound).Thermal extraction method of the present invention can be used for from biological material, extracting a cut in these compounds.A cut in these compounds comprises Xanthaurine, l-Epicatechol, proanthocyanidin, Citrus Vitamin P complex, catechin, trans-resveratrol, kaempferol, Vanillin and β-Gu Zaichun without limitation.For example, in an embodiment of the invention, from cocoa or contain the starting material of cocoa and extract l-Epicatechol.For example, flavonoids can be used as inhibitor and other purposes, such as being used in treatment or anti-curing cancers, heart trouble etc.For example and nonrestrictive, another source of flavonoids is for flax or contain the starting material of flax.One or more flavonoidss that can use flax to obtain to comprise to comprise catechin and l-Epicatechol according to heat extraction substrate of the present invention.Other also can obtain through utilizing heat to extract from the natural product that biomass extract, and can be used as medicine, natural additive etc.As another limiting examples, the starting material that contain coffee can be used for obtaining to comprise the heat extraction substrate of theine.
Obviously, concerning those of skill in the art, many other materials all maybe be for being used to obtain comprise the starting material that are fit to of the heat extraction substrate of one or more required compounds.
Starting material used in this invention also can reduce size.For example, before heat is extracted, can be used in method as known in the art its chopping is perhaps ground.
In an illustrative embodiments of the present invention, the size that at first will carry out the material that heat extracts is decreased to mean diameter on its minimum size less than about 2cm.In another illustrative embodiments of the present invention, at first raw-material size is reduced to mean diameter on its minimum size less than about 1cm.
Can in heat extraction system, carry out according to hot extraction of the present invention, to the not special restriction of this system.In heat of the present invention is extracted, can control with enclosed environment in will be raw-material all perhaps cuts be heated.For example, if starting material are biological materials, then can use cut xylogen, cellulosic or semicellulose or its compsn.The environment of control refers to a kind of like this environment; Wherein impelling starting material to undergo phase transition or the mode of chemical conversion applies heat, rather than with cause that quite a large amount of required compounds that are present in the starting material are changed nocuously, the mode of degraded, destruction etc. applies heat.For example, in one embodiment, said heat extraction substrate comprises the impurity that is converted into about 0～10%w/w (or its any subrange) that another kind of compound obtains from required compound with chemistry or alternate manner.
In an illustrative embodiments of the present invention, it is in comprising the heat extraction system of closed container, thermal source and one or more retrieving arrangements, to carry out that said heat is extracted.Can accomplish heat to starting material and any resulting intermediate product through conducting heat then extracts.Can starting material and any resulting intermediate product be heated to enough temperature and time enough to produce product stream like this, its cut can reclaim in one or more retrieving arrangements and collect to obtain extract then.
For example; Said hot extraction system can comprise standard destructive distillation system (stand retort system) (promptly; At vacuum or fixed bed under pressure or moving-bed), bubbling fluidized bed, the hot extraction element of upflowing, circulating fluidized bed, transmission bed, the extraction element hot in nature of ablating, the hot extraction element of air flow bed, rotary kiln or the hot extraction element of mechanical transmission (for example, heating spiral system).
Be collected in the product vapor of producing in the hot leaching process and any device of liquid and can be used as retrieving arrangement.Retrieving arrangement can comprise condensing surface.This condensing surface can be from steam cooling and collect the contact or the surface condenser of product liquid, perhaps also can be from steam cooling and the liquid quench of collecting product liquid.Retrieving arrangement also can comprise mist eliminator, fiber bed filter or other is with the device that comes to collect from vapour stream product liquid in the art.Retrieving arrangement can comprise one or more assemblies, for example, one or more can be with the condensing surface that is connected in series.
In an illustrative embodiments of the present invention, the enough heat of supply is producing the temperature in about 250 ℃～650 ℃ scopes in heat extraction system, or the temperature of its any subrange comprises, for example, about 300 ℃～550 ℃, perhaps about 320 ℃～400 ℃.The total residence time of material in heat extraction system can for, for example, be less than about 30 seconds, for example, in about 0.1～about 30 seconds scope, perhaps its any subrange.For example, in an illustrative embodiments, total residence time is about 0.2～about 5 seconds.In another illustrative embodiments, total residence time is about 2 seconds or still less.The residence time of the material in heat extraction system is to measure from the raw-material timed interval that is heated between the cancellation (for example cooling) heat extraction system.
Hot extraction can produce the product stream that comprises solid, liquid and/or steam.This product stream can be by fractionation to obtain cut, and said cut can be collected and obtain one or more extracts.Cut can be for example burnt solid, liquid and/or steam, or its combination.Can obtain to contain cut or its combination of the concentrated extract of required compound.Liquid and/or steam cut can comprise the required compound of greater concn usually than solid fraction.But, also can obtain solid fraction.For example; In the hot leaching process of Japanese yew biomass, any solid by-product possibly concentrated and be concentrated in to Taxan, on surface, matrix or the hole such as the carbon by product; This possibly cause being rich in the solid fraction of Taxan, and it can be collected to obtain the present invention and be rich in the extract of Taxan.
In an embodiment of the invention, obtain liquid distillate through condensation according to the steam that thermal extraction method of the present invention obtains.After from liquid, removing for example burnt solid and collect liquid and also can obtain liquid distillate to obtain according to extract of the present invention.The liquid distillate that after based on the extraction of the biological material of plant, obtains possibly be, for example, and tar, pitch, Wood vinegar mixture etc.
In thermal extraction method of the present invention, liquid and/or steam cut can be by further fractionation.Each the further cut that produces like this can be collected respectively to obtain a plurality of extracts, perhaps is collected and is merged into one or more extracts.Fractionation also can be used for selectivity production and be rich in selected compound, for example the extract of selected Taxan.
Extract of the present invention (this paper is also referred to as " heat extraction substrate ") can be for example collected solid, liquid and/or steam cut, or its any combination.Its also can be collected the cut of solid, liquid and/or steam cut, or the combination of the cut of selected collection.Can obtain single extract through collecting single cut or collecting and merge a plurality of cuts.Through collecting a plurality of cuts or also can obtaining a plurality of extracts through the cut of collecting a plurality of merging.And this extract possibly comprise or not comprise from raw-material phase transformation (for example, from the solid to liquid etc.).
It has been observed that other method of using that hot extraction can provide than in document, report, comprise the productive rate of the compound that is extracted that the productive rate of traditional solvent recuperation extraction and method of purification and other non-solvent processes is higher.
For example, it has been observed that and to obtain more total Taxan and the specific Taxan that comprises taxol of high yield through thermal extraction method.People also further notice, the extract that is rich in Taxan that obtains through thermal extraction method in given volume than the Taxan that has greater concn in isopyknic Cercocarpus or Australia Taxus solid biomass starting material or in initial (the first step) solvent extractable matter of isopyknic Cercocarpus or Australia Taxus biological material.
An implication of more spissated extract does; In order to reach the finished product of comparable measure, the situation of the volume ratio use solid material material of the material that in purification, separation and recovering step subsequently, need handle or the extract that from conventional solvent recovery process, obtains is littler.In order to obtain comparable productive rate, the original volume of having observed the extract after the enrichment of the present invention that in follow-up purification step, will be processed can be littler than the volume of the original material that in conventional solvent extraction process, need be processed, a for example little one magnitude.For example; Extract for Taxan; When comparing with the volume of the initial biological material that in conventional solvent extraction process, need be processed for the purifying Taxan that obtains comparable productive rate, hot extraction can be produced and reduced for example 10 times, 15 times, 25 times or 50 times or bigger multiple or the extract that is rich in Taxan of multiple volume therebetween.
Comprise the taxane compounds below one or more at the Taxan that possibly exist in the extract of Taxan that is rich in of the present invention: taxol; Taxol B; Baccatine III; 10-deacetylation taxol; 10-deacetylation Taxol B; 10-deacetylation crust card fourth III (having another name called 10-DAB or DAB); 13-ethanoyl-9-hydroxyl crust card fourth III (having another name called DHB); 7-xylosyl taxol; 7-xylosyl Taxol B; 7-xylosyl crust card fourth III; And verivate and analogue.This is enumerated and is non exhaustive.Other Taxan also possibly be present in the extract that is rich in Taxan of the present invention.
Except more than a kind of taxane compounds; Extract cut of producing and the extract that is rich in Taxan through heat and also possibly comprise many other components; Comprise depolymerization xylogen, fragmented Mierocrystalline cellulose-derived products and semicellulose-derived products; With other reactive component that comprises phenolic cpd, and many other components.
Observed the heat extraction and higher Taxan overall yield is provided than known Taxan recovery or working method, and the higher Taxan productive rate with present commercial value.Heat is extracted " fingerprint " of observed main Taxan component in the extract that obtains or the concentration of relative distribution and the Taxan in said extract also is different from the extract that obtains through present method passing through.For example; Compare with the average yield of in document, reporting that from the solvent extraction of Japanese yew needle and clipping, obtains; Observed taxol yield and can increase about 3 to about 5 times (promptly about 300 to about 500%); The DHB productive rate can increase about 2 to about 3 times (promptly about 200 to about 300%), and DAB increases about 8 times (promptly about 800%), and total Taxan productive rate can increase about 20 times (promptly about 2000%).
According to a theory of the present invention, it is not considered to limit scope of the present invention, thinks that heat extracts that discharged maybe be by Chemical bond or physical isolation (for example, in cellularstructure) thereby the compound that can not reclaim through solvent method.In these cases; When extracting free and available required compound, hot extraction of the present invention can be simultaneously through make reduction learn bond rupture and/or make any possibly isolate or stop to break with the physical structure of ordinary method extraction discharge and extract perhaps isolated compound of bonded.For example, when starting material were biomass, required compound possibly be included in the vacuole, and this vacuole can be extracted by heat and break discharging entire contents, can not take place usually thisly to break and discharge through using conventional process for extracting.
The extract of the present invention that includes, but are not limited to liquid, liquid distillate, solid and solid fraction can use the whole bag of tricks well known by persons skilled in the art further to handle to be commercial use purifying, segregation and recovery required compound.
For example; When reclaiming Taxan; The inventive method can further comprise with the extract that is rich in Taxan that is obtained and water or the contacted step of some other suitable dispensing solvents with further separate, segregation and concentrated Taxan component; The said extract that is rich in Taxan comprises, for example through all cuts, selected liquid distillate that merges collection that merges collection and the whole extract that merges the solid carbon cut acquisition of collecting.The adding of water or some other suitable dispensing solvents can directly take place (promptly in heat extraction system; Original position); Particularly in the product retrieving arrangement in the treating processes of biomass, perhaps as independent step or several steps after product is reclaimed from hot extraction process.
And for segregation from the component of other less needs and concentrated some required compound cut, thermal extraction method of the present invention can also comprise fractionating step.(for example, when extracting Taxan, some required Taxan can be separated from Taxan, phenolic cpd, lignocellulose, suppressor factor and other pollutent of less needs.) can carry out the non-removal that needs component to simplify follow-up purification step or to increase the economic worth of intermediate.
Use the isolation yield of the taxol that present organic solvent extraction technology obtains from the Japanese yew bark generally to be about 0.01%, and be about 0.003 to about 0.015% from clipping and needle.But, obtained about isolation yield of 0.031 to 0.049% with the inventive method.Isolation yield as from clipping and needle, obtain DHB through present organic solvent extraction technology is generally about 0.04%.But, obtained the segregation DHB productive rate between about 0.08 to 0.12% with the inventive method.Isolation yield as from clipping and needle, obtain DAB through present organic solvent extraction technology is generally about 0.06%.But, obtained the segregation DAB productive rate between about 0.46 to 0.53% with the inventive method.Productive rate as from clipping and needle, reclaim the total Taxan that obtains through present organic solvent extraction technology is generally about 0.25%.But, measured total Taxan productive rate 5 to 7% with the inventive method.
Heat is extracted and also can be used on the starting material that maybe be comprised the rough handling through solvent extraction.For example, observed and from new source or after solvent extraction, heat to have extracted theine.
Be suitable for preparing extract system according to the heat of one or more extracts of the present invention a case description at USP the 6th, 844, in No. 420 (Freel and Graham), its disclosure is hereby incorporated by, and is shown among Fig. 1.Concise and to the point; This system comprises feed system (10), closed container (20), particulate inorganic heating carrier reheat system (30) and the object of the invention in order to describe in this article, at least one retrieving arrangement; It is as seen in fig. 1; And also it is not considered to limit by any way the present invention, can comprise elementary (40) and secondary (50) condensing surface, and the product vapor stream that will in hot leaching process, produce through these condensing surfaces for example utilizes liquid quench (80) cooling and collection.Retrieving arrangement can comprise that also mist eliminator (60) and fiber bed filter (70) or other device are to collect product liquid.Heat of the present invention is extracted product component and can be derived from from least one retrieving arrangement; The selected product cut that obtains in for example elementary or secondary retrieving arrangement or its combination; Perhaps it can be all oil of from the firsts and seconds retrieving arrangement that comprises mist eliminator and fiber bed filter or its combination, obtaining (that is, all hot liquid product).But, should be appreciated that the retrieving arrangement that similarly comprises different numbers or size, or the heat of different condensing workss extract the selectivity preparation that system can be used as the extract of the object of the invention.
The retrieving arrangement system of in hot extraction reactor system, using of in Fig. 1, simply drawing, it is not considered to limit by any way the present invention, can comprise using direct liquid contact condenser (80) to come cooling heat to extract product.But, should be appreciated that any suitable retrieving arrangement that comprises surface condenser can use.In one embodiment, the liquid that is used for cooling heat extraction product that in these condensing surfaces (80), uses is from correspondingly cooled elementary or secondary condenser product (90) acquisition.But as being conspicuous that kind to those of skill in the art, any other compatible liquid that in primary and secondary retrieving arrangement or its combination, is used for cooled product also can be used for this purpose.And, other washer or comprise that the refrigerating unit of the heat exchanger that comprises solid surface etc. also can be used for cooled product steam, this also is considered within the scope of the invention.
A. the description of starting material-ground hemlock
Ground hemlock (Taxus canadensis Marsh, Canada yew, ground hemlock) shrub is that collect the holy Mary peripheral region (north latitude 46.34 degree, west longitude 84.17 degree) of between 7～September in 2004, reviving from the Ontario, Canada.The voucher specimen of compacting (2004-4001-10CFS-SSM#s) is left in Canadian forestry bureau-Su Sheng Mary herbarium with the ground hemlock (Taxus canadensis Marsh) of Ramulus et folium taxi cuspidatae-Taxaceae.Fresh ground hemlock (T.Canadensis) needle and sprig (twig) are in room temperature 22-24 ℃ air dried.Dried sample is grinding machine in the Thomas-Wiley laboratory, grinds to form～the 0.5mm particle size among the Model 4 (Thomas Scientific, the U.S.).
B. analytical procedure and program
The analysis of Taxan product
Use is equipped with Waters Delta Prep 4000 liquid chromatographs of computer and Empower software,
autoscan photodiode array Spectrophotometric Assays appearance and analytical column to carry out performance liquid chromatography.The analytical column that in the experiment that is described below, uses is Curosil-PFPPhenomenox (internal diameter 250x4.60mm).Use the acetonitrile/water solvent system at room temperature to adopt improved gradient chromatographic technique (Phenomenex).But, also used other solvent system.Use the suitable gradient of acetonitrile/water, for example 25/75 to 65/35 gradient surpass for some time of 40 minutes with the flow velocity of 1.0ml/min with the sample wash-out.Scan resolved peaks in wavelength 228nm place's detection compound and through photodiode array detector from 200 to 400nm.
(Waters EDGE) filters, and under the situation that adds and do not add standard substance, 10 μ l is injected in the HPLC post through 13mm GHP 0.45 μ m Minispike with the diluting soln (10mg/mL) of extract.Confirm the peak according to RT and UV spectrum.The reduction factor that use is obtained by commercially available Taxan standard substance will convert mg/ml into the peak height at the absorbance measuring at 228nm place.Such HPLC analyzes and repeats three times.
Record UV spectrum on ultraviolet-visible Beckman DU series 640 spectrophotometers.Utilize TLC and HPLC through identifying Taxan with the common-red, orange, green, blue, yellow (ROGBY) of standard model (ChromaDex, Santa Ana, California, the U.S.).
Embodiment 1: utilize heat to extract and produce heat extraction substrate
Basically as at USP the 6th, 844, that kind described in No. 420 (its disclosure is hereby incorporated by) will be handled in heat extraction system according to the Chinese hemlock spruce raw material of method for preparing.Be described below, in heat extraction system, burnt product and product vapor/air-flow sharp separation, and in elementary retrieving arrangement, utilize direct liquid contact condenser or liquid quench with product vapor and the liquid fast quench that discharges.The compound that is retained in the product vapor is transferred to the secondary retrieving arrangement that is connected with elementary retrieving arrangement with series system.In this secondary retrieving arrangement, utilize direct liquid contact condenser or liquid quench with the product vapor quenching then, and collect the product of condensation.Any resultant product in product vapor is collected (see figure 1) in mist eliminator and filter bed.Collect elementary retrieving arrangement product and secondary retrieving arrangement product.The productive rate of the product liquid that obtains from retrieving arrangement is about 40 to the scope of about 60% (w/w), and is generally about 49% (see figure 1).
Embodiment 1A: heat is extracted test 1
In adopting 490 ℃ up-flow reactor (see figure 1) of surface condenser, will contain 2.52wt% ash content and 8.73wt% moisture the Chinese hemlock spruce raw material (4,715g) carry out the heat extraction and produce the thing oil samples next life.Liquid yield based on " ashless (ash free) " charging is 55.49wt%.The heat extraction substrate sample that carries out the Taxan analysis comprises aqueous distillate (1024.5g), tarry cut (440.5g) and the neat liquid cut of extruding from the glass fiber filter material mist eliminator (170g).
Embodiment 1B: heat is extracted test 2
In 398 ℃ up-flow reactor (see figure 1), will contain with the surface condensation mode operation 1.80wt% ash content and 5.20wt% moisture the Chinese hemlock spruce raw material (7,996g) carry out heat and extract production fluid body heat extract in next life.Liquid yield based on " ashless " charging is 45.12wt%, and Jiao is 17.41wt% for 28.54wt% gas.
Get the sample of the heat extraction substrate that contains Taxan and carry out the Taxan analysis.
In this embodiment, compare with the original volume of the biomass of producing extract, the volume of heat extraction substrate has reduced by about 25 times (initial solvent without any need for solid biomass is extracted).
Embodiment 1C: heat is extracted test 3 (see figure 2)s
397 ℃ down and will contain in the up-flow reactor (see figure 1) with the liquid quench mode operation 1.80wt% ash content and 5.20wt% moisture the Chinese hemlock spruce raw material (5,641g) carry out heat extraction production fluid body heat in next life extraction sample.Said quench liquid is the aquatic products thing that from the test of embodiment 1A, obtains and about 50/50 mixture of softening water.Liquid yield based on " ashless " charging is 46.77wt%, and Jiao is 19.0wt% for 25.87wt% gas.The purpose of this test is the product productive rate that relatively utilizes product productive rate that liquid quench obtains and surface condensation to obtain.
Getting the heat that contains Taxan extracts the sample of product and carries out the Taxan analysis.
In this embodiment, compare with the original volume of the biomass of producing extract, the volume of heat extraction substrate has reduced by about 50 times (initial solvent without any need for solid biomass is extracted).
Embodiment 1D: the selectivity fractionation of the Taxan in recovery system
The heat that the selectivity fractionation of the Taxan in recovery system and the demonstration of spissated instance are described in 1B is extracted among the embodiment.In this instance, in the heat extraction substrate cut that from the fibre bed filtering recovering device, reclaims, detect about taxane content discerned of 50%, though only accounting in heat, this cut extracts 22% of total heat extraction substrate of producing in test 2 processes.
Embodiment 1E: the further selectivity fractionation of the Taxan in recovery system
Distribute the further selectivity fractionation of solvent and heat that spissated embodiment demonstration is described in 1C to extract among the embodiment through adding entry or other.In this instance; Ground original position in recovery system adds water; And the result detects about taxane content discerned of 50% in the heat extraction substrate cut that from the fibre bed filtering recovering device, reclaims, and extracts 24% of total heat extraction substrate of producing in test 3 processes though this cut only accounts in heat.Except adding entry and direct heat of condensation extract product, the hot extraction conditions of test 3 aspect temperature and treatment time with to test 2 identical.Therefore, when with as when under test 2 situation, not having the selectivity fractionation of the Taxan of water dispenser to compare, in test 3, utilize the selectivity fractionation of the Taxan of water dispenser to be shown as more effective.
The analysis of embodiment 1A, 1B and 1C: in the qualitative analysis that obtains Taxan, use and utilize silica gel and with 95: 5 methylene dichloride: methyl alcohol is as the tlc (TLC) of the heat extraction substrate of solvent and prove useful (that is, there is Taxan in confirmation in sample).The result that TLC analyzes is listed in last row of table 1 (also promptly, Taxan being reported as " measuring " or " not measuring ").
Embodiment 2: the segregation and the quantitative analysis of the Taxan through gel chromatography and HPLC
Isolation process 1: the polyvinylpolypyrrolidone that will mix and be adsorbed on 1g like the heat extraction substrate sample (1g) that summarizing among embodiment 1A, 1B and the 1C, obtains; PVPP (sigma chemical company; P-6755 [25249-54-1]) on; And be applied among the strata-X 33 μ m Polymeric Sorbent lg/20ml GigaTubes (Phenomenex, 8B-S 100-JEG).Before loading above-mentioned sample, adapt to strata-X and use the 20mL deionized water balance with 20mL methyl alcohol.Utilize following solvent system to carry out wash-out at a slow speed.
A) methyl alcohol-deionized water (7: 3) [5x 12mL]
B) methyl alcohol: acetonitrile: deionized water (6: 3: 1), (6: 2: 2) perhaps (5: 2: 3) [5x 12ml] and
C) methyl alcohol: acetonitrile (1: 1) [5x 12mL].
Use TLC and HPLC that the cut that is rich in Taxan is carried out stratographic analysis.TLC is used for qualitative analysis (table 1) and HPLC is used for quantitative analysis to measure the total Taxan and the independent productive rate (table 1,2 and 3) of Taxan.Solvent system " b " (6: 3: 1) is chosen as the active solvent of quantitatively determined Taxan productive rate, and uses this solvent system to be determined at the productive rate of reporting in the table.
Table 1:TLC and HPLC analyze
Solvent system A. methyl alcohol: deionized water (7: 3)
Solvent system B. methyl alcohol: acetonitrile: deionized water (6: 3: 1)
Solvent system C. methyl alcohol: acetonitrile (1: 1)
N.D.=does not measure
The Taxan of trace=trace
As extracting production via heat and utilizing the total Taxan of isolation process 1 recovery and the productive rate of independent Taxan component to be reported in respectively in the table 2 and 3.In table 2, also provided the document (Daoust for example of total " isolation process 1 " Taxan productive rate and conventional method for recovering solvents; G and Sirois; G.; 2003 with " Canada Yew (Taxus canadensis Marsh.) and Taxanes:A Perfect Species for Filed Production and improvement Through Genetic Selection " Natural Resources Canada; Canadian Forest Service, Sainte-Foy, Quebec) comparison of the productive rate of middle report.In table 3, also provided the comparison of " isolation process 1 " productive rate and the solvent control test productive rate of each representative Taxan.
Data from table 2 and 3 can be found out, use the total Taxan of the inventive method and the productive rate of each representative Taxan to be higher than the productive rate that uses conventional solvent-extraction process to obtain.
Table 2: extract " isolation process 1 " productive rate of the total Taxan that obtains and the comparison of conventional solvent productive rate (as reporting among the document *) via heat
*Daoust，G?and?Sirois，G.，2003，″Canada?Yew(Taxus?canadensis?Marsh.)and?Taxanes：A?Perfect?Species?for?Filed?Production?and?improvement?Through?Genetic?Selection″Natural?Resources?Canada，Canadian?Forest?Service，Sainte-Foy，Quebec
Table 3: extract taxol and " isolation process 1 " productive rate of other other taxane compounds and the comparison of solvent extraction (solvent control *) productive rate that obtains via heat
* see embodiment 3
Isolation process 2: the polyvinylpolypyrrolidone that will mix and be adsorbed on 1g like the heat extraction substrate sample (1g) that summarizing among embodiment 1A, 1B and the 1C, obtains; PVPP (sigma chemical company; P-6755 [25249-54-1]) go up and be applied to strata-X 33 μ m Polymeric Sorbent lg/20ml GigaTubes (Phenomenex, 8B-S100-JEG) in.Before loading above-mentioned sample, adapt to strata-X and use the 20mL deionized water balance with 20mL methyl alcohol.The aliquot that increases (20,50,70,100%) gradually with methanol concentration subsequently with 20mL water is to carry out wash-out at a slow speed.Maximum concentration in the cut with the 50-70% methanol-eluted fractions, to find carries out stratographic analysis to all cuts.
Embodiment 3
The solvent extraction of Taxan (non-pyrolysis controlled trial)
(4417.13g fresh weight (fr.wt)) at room temperature extracts with two steps with fresh ground hemlock needle: the first step, in 100% methyl alcohol (1g fresh weight/10ml solvent), soak 24h, and chopping and decant go out solvent in commercially available Waring blender subsequently; In second step, the residue after the chopping is soaked 24h again in 60% aqueous methanol.With the methanol extract reduction vaporization after merging until removing great majority or all methyl alcohol.The lyophilize resistates obtains the crude extract of 713.88g.From the needle of every g fresh weight, obtained the ground hemlock crude extract of 162mg like this.This test-results provides in table 3 with " solvent control ".
Embodiment 4
Under 464 ℃ temperature and in the up-flow reactor (see figure 1) of liquid quench mode operation the coffee raw material after the solvent extraction is carried out heat, extract to produce the heat extraction substrate sample.Liquid yield based on " ashless " charging is 55.15wt%, and coke yield is 16.87wt% and gas yield is 24.37wt%.The purpose of this test is whether to measure any remaining theine that can heat extract in the coffee raw material that remains in after the solvent extraction.
Get the heat extraction substrate sample that contains theine, and computer is housed in use and Chem.Station software (Chem.32), Binary pump SL (G1312B), high efficiency automatic trier SL (G1367C) and autoscan photodiode array Spectrophotometric Assays appearance Agilent (Agilent Technologies) Agilent 1200 liquid chromatographs (G1315C) carry out the theine analysis.
The result:
R158A mist eliminator terepthaloyl moietie: in the oil of 1g, contain the 91.2ppm theine
The R158A primary condenser contains the 129ppm theine in the oil of 1g
Embodiment 5
Under 500 ℃ temperature and in the up-flow reactor (see figure 1) of liquid quench mode operation flax curst (flax shive) raw material is carried out heat, extract to produce the heat extraction substrate sample.Liquid yield based on " ashless " charging is 55.57wt%, and coke yield is 14.48wt%, and gas yield is 23.61wt%.The purpose of this test is to measure whether can heat extract any l-Epicatechol and the catechin in flax curst.
Get collection heat of liquid extract product sample and use Agilent Eclipse Plus C-185 μ m (4.6x 150mm internal diameter) anti-phase analytical column to carry out l-Epicatechol and catechin analysis.At room temperature use the gradient chromatographic technique: solvent orange 2 A=methyl alcohol/acetonitrile (95: 5); The solvent B=0.05%HCOOH aqueous solution; Flow velocity is 0.9ml/min.Use three definite detection wavelength: 270nm, 280nm and 350nm, and resolved peak scans from 250 to 400nm with photodiode array detector.
The result:
■ detects l-Epicatechol and catechin with sizable amount
Though in order to understand clearly purpose; Explanation and embodiment and the one or more embodiments of reference have described in detail foregoing invention by way of example; But under situation about not departing from like the essence of the present invention in accompanying claims, described and scope; To those skilled in the art, according to instruction of the present invention, obviously can carry out some variation, change and improvement to the present invention.
Must be pointed out that only if clear in addition indicating in the context, the singulative that in the English edition of this PCT specification sheets and accompanying claims thereof, uses " a ", " an " and " the " comprise plural.
Only if definition is arranged in addition, the common sense of the those of ordinary skill under all technology used herein and scientific terminology and the present invention in the field has identical meaning.
All publications, patent and the patented claim of in present specification, quoting all are hereby incorporated by, as each independent publication, patent or patented claim all especially with indicate respectively be introduced into the same as a reference.Quoting of any publication, patent or patented claim is not to admit that this publication, patent or patented claim are prior art in present specification.
Claims (20)
1. one kind is extracted the method for producing the heat extraction substrate that is rich in Taxan through the raw-material heat of the biomass that contain diterpene-kind compound, comprising:
The said biomass starting material that contain diterpene-kind compound are heated to about 250 ℃ of extremely about 650 ℃ temperature stops are less than about 30 seconds time; Wherein this heating process enough extracts a certain amount of taxane compounds and taxane compounds and is not converted into one or more other compound from starting material, and the wherein said heat extraction substrate that is rich in Taxan comprises one or more other the compound that is less than about 10 weight %.
2. according to the process of claim 1 wherein, said starting material derive from yew tree.
3. according to the process of claim 1 wherein, said heat extraction substrate comprises one or more other the compound that is less than 0.5 weight %.
4. according to the process of claim 1 wherein, compare with starting material, said heat is extracted the volume that causes heat extraction substrate and is reduced 10 times, 20 times or 50 times.
5. one kind is extracted the method for from these biomass starting material, producing the heat extraction substrate that is rich in Taxan through the raw-material heat of the biomass that contain diterpene-kind compound, comprising:
Said biomass starting material are heated to about 300 ℃ of extremely about 550 ℃ temperature stops are less than about 5 seconds time; Wherein this heating process enough extracts a certain amount of taxane compounds and taxane compounds and is not converted into one or more other compound from starting material, and the wherein said heat extraction substrate that is rich in Taxan comprises one or more other the compound that is less than about 5 weight %.
6. according to the method for claim 5, wherein, said biomass starting material comprise the kind of Cercocarpus or Australia Taxus.
7. the method for the heat extraction substrate of Taxan is rich in a production, comprising:
The starting material that will contain diterpene-kind compound add and comprise in the heat extraction system of closed container, thermal source and at least one retrieving arrangement;
In this heat extraction system, the said biomass starting material that contain diterpene-kind compound are heated to about 250 ℃ of extremely about 650 ℃ temperature stops and are less than about 30 seconds time; Wherein this heating process enough produces the product stream that comprises a certain amount of taxane compounds and taxane compounds and is not converted into one or more other compound, and the wherein said heat extraction substrate that is rich in Taxan comprises one or more other the compound that is less than about 10 weight %; With
In at least one device of at least one retrieving arrangement, collect at least one cut to obtain to be rich in the heat extraction substrate of Taxan from the product stream that is rich in taxane compounds.
8. according to the method for claim 7, wherein, said starting material are the biomass starting material that contain diterpene-kind compound that comprise the kind of Cercocarpus or Australia Taxus.
9. according to the method for claim 7, wherein, said thermal source in heat extraction system, produce about 320 ℃ to about 400 ℃ temperature.
10. according to the method for claim 7, wherein, the residence time of said starting material in heat extraction system is less than about 2 seconds.
11. according to the method for claim 7, wherein, in joining hot extraction system before, said raw-material size is reduced to mean diameter on its smallest dimension less than about 2cm.
12. according to the said method of claim 7, wherein, said heat extraction substrate comprises one or more other the compound that is less than 0.5 weight %.
13. method according to claim 7; Wherein, The said at least a cut of collecting from product stream is selected from the burnt cut of the solid that contains Taxan, the liquid distillate that contains Taxan, the steam cut that contains Taxan and their mixture; Wherein when collecting more than a kind of cut, merge collected cut to obtain being rich in the heat extraction substrate of Taxan.
14. method according to claim 13; Wherein, Perhaps collect the steam cut that contains Taxan in more a plurality of retrieving arrangements at two; And randomly, at least one in wherein said two or the more a plurality of retrieving arrangements contains from the device of steam fraction collection liquid distillate, and the device of wherein said collection liquid distillate is condensing surface, mist eliminator, fibre bed strainer or its combination.
15. according to the method for claim 14, wherein, each collected cut all is the heat extraction substrate that is rich in Taxan.
16. according to the method for claim 13, wherein, collected liquid distillate is the heat extraction substrate that is rich in Taxan.
17. method according to claim 13; It comprises further handles the said heat extraction substrate that is rich in Taxan with one or more Taxans of selective removal; Wherein should further handle the optional distribution solvent that comprises; This distribution solvent can comprise water, with one or more Taxans of selective removal.
18. method according to claim 7; Wherein, Said at least one cut that contains Taxan of fractionation is to obtain further cut in collection process, and said further cut is collected respectively, and wherein obtains being rich in the heat extraction substrate of Taxan from least one said further cut.
19. according to the method for claim 18, wherein,
(a) the further cut of each collection all is the heat extraction substrate that is rich in Taxan; And/or
(b) with distributing solvent, this distribution solvent can comprise water, handles one or more collected further cuts.
20. a heat extraction substrate, wherein said heat extraction substrate is:
A kind of extract that contains taxol and 10-O-deacetylation crust card fourth III, wherein, based on weight ratio, much about 10 times of the amounts of the 10-O-deacetylation crust card fourth III that in this extract, exists than the amount of taxol;
A kind of extract that contains taxol and 13-ethanoyl-9-hydroxyl crust card fourth III, wherein, based on weight ratio, much about 10 times of the amounts of the 13-ethanoyl that in this extract, exists-9-hydroxyl crust card fourth III than the amount of taxol; Or
A kind of extract that contains taxol and 7-table-taxol, wherein, based on weight ratio, much about 10 times of the amounts of the 7-table-taxol that in this extract, exists than the amount of taxol.
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Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2647564C (en) * | 2006-04-03 | 2016-08-30 | Pharmatherm Chemicals Inc. | Thermal extraction method and product |
| US20110284359A1 (en) | 2010-05-20 | 2011-11-24 | Uop Llc | Processes for controlling afterburn in a reheater and for controlling loss of entrained solid particles in combustion product flue gas |
| US8499702B2 (en) | 2010-07-15 | 2013-08-06 | Ensyn Renewables, Inc. | Char-handling processes in a pyrolysis system |
| US8906236B2 (en) | 2010-07-26 | 2014-12-09 | Sapphire Energy, Inc. | Process for the recovery of oleaginous compounds and nutrients from biomass |
| US9028696B2 (en) | 2010-07-26 | 2015-05-12 | Sapphire Energy, Inc. | Process for the recovery of oleaginous compounds from biomass |
| CN104087350A (en) | 2010-07-26 | 2014-10-08 | 蓝宝石能源公司 | Process for the recovery of oleaginous compounds from biomass |
| US9441887B2 (en) | 2011-02-22 | 2016-09-13 | Ensyn Renewables, Inc. | Heat removal and recovery in biomass pyrolysis |
| US9347005B2 (en) | 2011-09-13 | 2016-05-24 | Ensyn Renewables, Inc. | Methods and apparatuses for rapid thermal processing of carbonaceous material |
| US9109177B2 (en) | 2011-12-12 | 2015-08-18 | Ensyn Renewables, Inc. | Systems and methods for renewable fuel |
| US9670413B2 (en) | 2012-06-28 | 2017-06-06 | Ensyn Renewables, Inc. | Methods and apparatuses for thermally converting biomass |
| CN103808851A (en) * | 2012-11-15 | 2014-05-21 | 刘胜远 | Thin-layer chromatography detection method of xylosyl-10-deacetyltaxol in taxus chinensis |
| EP3492559A1 (en) | 2013-06-26 | 2019-06-05 | Ensyn Renewables, Inc. | Methods for renewable fuel |
| US20180179447A1 (en) * | 2015-06-12 | 2018-06-28 | Netternergy B.V. | System and method for the conversion of biomass, and products thereof |
| EP3337966B1 (en) | 2015-08-21 | 2021-12-15 | Ensyn Renewables, Inc. | Liquid biomass heating system |
| US10400176B2 (en) | 2016-12-29 | 2019-09-03 | Ensyn Renewables, Inc. | Demetallization of liquid biomass |
| EP4081613A1 (en) | 2019-12-23 | 2022-11-02 | Kerry Luxembourg S.a.r.l. | Methods for formaldehyde control |
| CN114773158A (en) * | 2022-04-26 | 2022-07-22 | 云南七丹药业股份有限公司 | Extraction process and production method of effective components of fresh pseudo-ginseng flower |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1300966A (en) * | 1970-03-10 | 1972-12-29 | Yoshizo Sakamoto | Methods for processing medicinal plants and herbs |
| US5395455A (en) * | 1992-03-10 | 1995-03-07 | Energy, Mines And Resources - Canada | Process for the production of anhydrosugars from lignin and cellulose containing biomass by pyrolysis |
| US6002025A (en) * | 1999-02-24 | 1999-12-14 | Bcm Developement Inc. | Method for the purification of taxanes |
| WO2001009243A1 (en) * | 1999-07-29 | 2001-02-08 | Ensyn Group, Inc. | Novel natural resin formulations |
| CN1362959A (en) * | 2000-02-02 | 2002-08-07 | 佛罗里达州立大学研究基金有限公司 | C10 carbamoyloxy substituted taxanes as antitumor agents |
| CA2521829A1 (en) * | 2004-09-30 | 2006-03-30 | University Of Ottawa | Process for extracting taxanes |
Family Cites Families (410)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2318555A (en) | 1943-05-04 | Cleansing agent and the | ||
| US1252072A (en) | 1916-09-13 | 1918-01-01 | William George Abbott Jr | Apparatus for cleaning the interior of tubular members. |
| US2205757A (en) | 1937-09-18 | 1940-06-25 | Standard Oil Dev Co | Coke cleaning apparatus |
| US2326525A (en) | 1940-08-28 | 1943-08-10 | Standard Oil Co | Method of preventing deleterious coke deposits |
| US2328202A (en) | 1940-12-30 | 1943-08-31 | Henry A Doerner | Process for producing magnesium metal |
| FR879606A (en) | 1941-10-27 | 1943-03-01 | Method and apparatus for treating gas from gasifiers | |
| US2380098A (en) | 1943-01-23 | 1945-07-10 | Henry A Doerner | Automatic reamer |
| US2492948A (en) | 1945-10-05 | 1950-01-03 | Universal Oil Prod Co | Controlling catalyst regeneration temperature |
| US2566353A (en) | 1948-08-04 | 1951-09-04 | Houdry Process Corp | Purification of oils |
| US2696979A (en) | 1951-04-16 | 1954-12-14 | Kennecott Copper Corp | Automatic tuyere punching apparatus |
| US2884303A (en) | 1956-03-06 | 1959-04-28 | Exxon Research Engineering Co | High temperature burning of particulate carbonaceous solids |
| US3130007A (en) | 1961-05-12 | 1964-04-21 | Union Carbide Corp | Crystalline zeolite y |
| GB1019133A (en) | 1962-09-12 | 1966-02-02 | Exxon Research Engineering Co | Hydrocarbon separation process for removal of impurities |
| US3313726A (en) | 1963-06-24 | 1967-04-11 | Monsanto Co | Process for regenerating ion exchange resins |
| US3309356A (en) | 1965-07-06 | 1967-03-14 | Weyerhaeuser Co | Separating levoglucosan and carbohydrate acids from aqueous mixtures containing the same-by solvent extraction |
| FI46091C (en) | 1966-06-15 | 1972-12-11 | Ahlstroem Oy | A way to heat treat mash or a similar substance. |
| US3467502A (en) | 1966-10-12 | 1969-09-16 | Continental Carbon Co | Feedstock control system for carbon black reactors |
| BE759016A (en) | 1969-12-18 | 1971-04-30 | Deggendorfer Werft Eisenbau | COOLER FOR THE PASSAGE OF AN ADJUSTABLE PART OF A HEAT VEHICLE KEEPED IN CIRCULATION IN A REACTOR |
| US3776533A (en) | 1970-01-28 | 1973-12-04 | Dravo Corp | Apparatus for continuous heat processing of ore pellets |
| US3696022A (en) | 1970-07-27 | 1972-10-03 | Universal Oil Prod Co | Swing-bed guard chamber in hydrogenerating and hydrorefining coke-forming hydrocarbon charge stock |
| US3694346A (en) | 1971-05-06 | 1972-09-26 | Exxon Research Engineering Co | Integrated fluid coking/steam gasification process |
| US3925024A (en) | 1971-09-10 | 1975-12-09 | Borden Inc | Grid burner system |
| US4039290A (en) | 1972-05-15 | 1977-08-02 | Kureha Kagaku Kogyo Kabushiki Kaisha | Spent activated carbon regenerator |
| US3959420A (en) | 1972-05-23 | 1976-05-25 | Stone & Webster Engineering Corporation | Direct quench apparatus |
| US3853498A (en) | 1972-06-28 | 1974-12-10 | R Bailie | Production of high energy fuel gas from municipal wastes |
| US3814176A (en) | 1973-01-22 | 1974-06-04 | R Seth | Fixed-fluidized bed dry cooling tower |
| US3907661A (en) | 1973-01-29 | 1975-09-23 | Shell Oil Co | Process and apparatus for quenching unstable gas |
| US3876533A (en) | 1974-02-07 | 1975-04-08 | Atlantic Richfield Co | Guard bed system for removing contaminant from synthetic oil |
| US3890111A (en) | 1974-02-21 | 1975-06-17 | Exxon Research Engineering Co | Transfer line burner system using low oxygen content gas |
| US3927996A (en) | 1974-02-21 | 1975-12-23 | Exxon Research Engineering Co | Coal injection system |
| US4052265A (en) | 1974-07-26 | 1977-10-04 | Kemp Klaus M | Process for the pyrolytic treatment of organic, pseudo-organic and inorganic material |
| US4032305A (en) | 1974-10-07 | 1977-06-28 | Squires Arthur M | Treating carbonaceous matter with hot steam |
| US4003829A (en) | 1975-02-10 | 1977-01-18 | Atlantic Richfield Company | Method of removing contaminant from a hydrocarbonaceous fluid |
| US4064043A (en) | 1975-02-18 | 1977-12-20 | Rohm And Haas Company | Liquid phase adsorption using partially pyrolyzed polymer particles |
| US4153514A (en) | 1975-02-27 | 1979-05-08 | Occidental Petroleum Corporation | Pyrolysis process for solid wastes |
| US4101414A (en) | 1975-09-02 | 1978-07-18 | Unitech Chemical Inc. | Rerefining of used motor oils |
| US4165717A (en) | 1975-09-05 | 1979-08-28 | Metallgesellschaft Aktiengesellschaft | Process for burning carbonaceous materials |
| CA1081466A (en) | 1976-03-26 | 1980-07-15 | David S. Mitchell | Countercurrent plug-like flow of two solids |
| US4085030A (en) | 1976-06-25 | 1978-04-18 | Occidental Petroleum Corporation | Pyrolysis of carbonaceous materials with solvent quench recovery |
| US4064018A (en) | 1976-06-25 | 1977-12-20 | Occidental Petroleum Corporation | Internally circulating fast fluidized bed flash pyrolysis reactor |
| US4145274A (en) | 1976-06-25 | 1979-03-20 | Occidental Petroleum Corporation | Pyrolysis with staged recovery |
| US4102773A (en) | 1976-06-25 | 1978-07-25 | Occidental Petroleum Corporation | Pyrolysis with cyclone burner |
| GB1561237A (en) | 1976-09-22 | 1980-02-13 | Ahlstroem Oy | Method of treating materials in a fluidized bed reactor |
| US4210492A (en) | 1977-03-14 | 1980-07-01 | Shell Oil Company | Process for the pyrolysis of coal in dilute- and dense-phase fluidized beds |
| JPS53116314A (en) | 1977-03-19 | 1978-10-11 | Mitsui Petrochem Ind Ltd | Separation of acetic acid and water |
| US4138020A (en) | 1977-05-13 | 1979-02-06 | Foster Wheeler Energy Corporation | Regeneration flow distribution device |
| US4103902A (en) | 1977-08-16 | 1978-08-01 | Foster Wheeler Energy Corporation | Water seal for regenerator |
| US4344770A (en) | 1977-11-04 | 1982-08-17 | Wilwardco, Inc. | Method and apparatus for converting solid organic material to fuel oil and gas |
| US4298453A (en) | 1977-12-27 | 1981-11-03 | Mobil Oil Corporation | Coal conversion |
| US4284616A (en) | 1978-02-15 | 1981-08-18 | Intenco, Inc. | Process for recovering carbon black and hydrocarbons from used tires |
| US4245693A (en) | 1978-10-11 | 1981-01-20 | Phillips Petroleum Company | Waste heat recovery |
| US4219537A (en) | 1978-10-31 | 1980-08-26 | Foster Wheeler Energy Corporation | Desulfurization and low temperature regeneration of carbonaceous adsorbent |
| US4300009A (en) | 1978-12-28 | 1981-11-10 | Mobil Oil Corporation | Conversion of biological material to liquid fuels |
| US4233119A (en) | 1979-01-23 | 1980-11-11 | Louis A. Grant, Inc. | Ascension pipe and elbow cleaning apparatus |
| IT1112472B (en) | 1979-04-09 | 1986-01-13 | Trojani Ing Benito Luigi | TUBE WITH INTERNAL FINISHING AND EXTERNAL FINISHING OR PINING, IN PARTICULARLY FOR HEAT EXCHANGERS, AND ITS MANUFACTURING METHOD |
| US4334893A (en) | 1979-06-25 | 1982-06-15 | Exxon Research & Engineering Co. | Recovery of alkali metal catalyst constituents with sulfurous acid |
| US4272402A (en) | 1979-07-16 | 1981-06-09 | Cosden Technology, Inc. | Process for regenerating fluidizable particulate cracking catalysts |
| US4225415A (en) | 1979-08-10 | 1980-09-30 | Occidental Petroleum Corporation | Recovering hydrocarbons from hydrocarbon-containing vapors |
| US4341598A (en) | 1979-08-14 | 1982-07-27 | Occidental Research Corporation | Fluidized coal pyrolysis apparatus |
| ZA807805B (en) | 1979-12-14 | 1982-01-27 | Energy Resources Co Inc | Fluidized-bed process to convert solid wastes to clean energy |
| JPS591758B2 (en) | 1980-01-18 | 1984-01-13 | 工業技術院長 | Gas treatment method for pyrolysis equipment |
| US4456504A (en) | 1980-04-30 | 1984-06-26 | Chevron Research Company | Reactor vessel and process for thermally treating a granular solid |
| US4301771A (en) | 1980-07-02 | 1981-11-24 | Dorr-Oliver Incorporated | Fluidized bed heat exchanger with water cooled air distributor and dust hopper |
| US4324641A (en) | 1980-08-26 | 1982-04-13 | Occidental Research Corporation | Pyrolysis process utilizing a beneficially reactive gas |
| US4324642A (en) | 1980-08-26 | 1982-04-13 | Occidental Research Corporation | Pyrolysis process for producing condensed stabilized hydrocarbons utilizing a beneficially reactive gas |
| US4324637A (en) | 1980-08-26 | 1982-04-13 | Occidental Research Corporation | Pyrolysis process with feed pretreatment utilizing a beneficially reactive gas |
| US4324644A (en) | 1980-08-26 | 1982-04-13 | Occidental Research Corporation | Pyrolysis process for stabilizing volatile hydrocarbons utilizing a beneficially reactive gas |
| US4308411A (en) | 1980-08-28 | 1981-12-29 | Occidental Research Corporation | Process for converting oxygenated hydrocarbons into hydrocarbons |
| US4317703A (en) | 1980-12-03 | 1982-03-02 | American Can Company | Pyrolysis process utilizing pyrolytic oil recycle |
| US4321096A (en) | 1980-12-16 | 1982-03-23 | John B. Pike & Son, Inc. | Apparatus and method for cleaning an explosion sensing port |
| US4325327A (en) | 1981-02-23 | 1982-04-20 | Combustion Engineering, Inc. | Hybrid fluidized bed combuster |
| US4336128A (en) | 1981-06-01 | 1982-06-22 | Chevron Research Company | Combustion of pyrolyzed carbon containing solids in staged turbulent bed |
| US4415434A (en) | 1981-07-21 | 1983-11-15 | Standard Oil Company (Ind.) | Multiple stage desalting and dedusting process |
| US4373994A (en) | 1981-09-28 | 1983-02-15 | Occidental Research Corporation | Pyrolysis process and apparatus |
| US4422927A (en) | 1982-01-25 | 1983-12-27 | The Pittsburg & Midway Coal Mining Co. | Process for removing polymer-forming impurities from naphtha fraction |
| JPS58150793U (en) | 1982-04-02 | 1983-10-08 | 日本鋼管株式会社 | Sintering raw material sampler |
| US4495056A (en) | 1982-04-16 | 1985-01-22 | Standard Oil Company (Indiana) | Oil shale retorting and retort water purification process |
| FR2526182B1 (en) | 1982-04-28 | 1985-11-29 | Creusot Loire | METHOD AND DEVICE FOR CONTROLLING THE TEMPERATURE OF A FLUIDIZED BED |
| US4931171A (en) | 1982-08-03 | 1990-06-05 | Phillips Petroleum Company | Pyrolysis of carbonaceous materials |
| DE3230656A1 (en) | 1982-08-18 | 1984-02-23 | Uhde Gmbh, 4600 Dortmund | METHOD FOR REHEATING AND PROMOTING A GRAINED HEAT CARRIER, AND DEVICE IN PARTICULAR FOR IMPLEMENTING IT |
| US4482451A (en) | 1982-09-16 | 1984-11-13 | Uop Inc. | Process for the separation of particulate solids from vapors using a discharge having a helical twist |
| EP0105980B1 (en) | 1982-10-06 | 1986-01-29 | Uop Inc. | Fluid particle backmixed cooling process and apparatus |
| US4434726A (en) | 1982-12-27 | 1984-03-06 | Combustion Engineering, Inc. | Fine particulate feed system for fluidized bed furnace |
| JPS58150793A (en) | 1983-01-17 | 1983-09-07 | Hitachi Ltd | Heat recovery device |
| US4443229A (en) | 1983-01-31 | 1984-04-17 | Chevron Research Company | Gasification process for carbonaceous materials |
| FR2540739A1 (en) | 1983-02-11 | 1984-08-17 | Elf France | DEVICE AND FACILITIES FOR THIN-FILM EVAPORATION DISTILLATION, ESPECIALLY FOR HYDROCARBONS, AND METHOD OF IMPLEMENTING SAID DEVICE |
| FR2541435B1 (en) | 1983-02-21 | 1986-10-17 | Elf France | THERMAL GENERATOR FOR PERFORMING THE HEATING OF FLUID BY THERMAL EXCHANGE USING A FLUIDIZED BED AND THE METHOD FOR ITS IMPLEMENTATION |
| US4897178A (en) | 1983-05-02 | 1990-01-30 | Uop | Hydrocracking catalyst and hydrocracking process |
| FR2548208B1 (en) | 1983-06-30 | 1987-01-09 | Inst Francais Du Petrole | PROCESS FOR THE MANUFACTURE OF SOLID FUELS FROM HEAVY OILS OF HYDROCARBONS AND VEGETABLE MATERIALS |
| BR8304158A (en) | 1983-07-26 | 1984-07-31 | Cia Agricolas E Florestal Sant | RECOVERY PROCESS OF LIGHT ALCATRATION, VOLATIZED IN BIOMASS PIROLYSIS IN DISCONTINUED CARBONIZATION OVENS AND THEIR INSTALLATION |
| US4504379A (en) | 1983-08-23 | 1985-03-12 | Exxon Research And Engineering Co. | Passivation of metal contaminants in cat cracking |
| BR8304794A (en) | 1983-09-02 | 1985-04-09 | Petroleo Brasileiro Sa | PROCESS FOR THE PRODUCTION OF OCTANAGE CAN GASOLINE |
| FR2563118B1 (en) | 1984-04-20 | 1987-04-30 | Creusot Loire | PROCESS AND PLANT FOR TREATING FLUIDIZED BED MATERIAL |
| DE3426080C2 (en) | 1984-07-14 | 1996-09-19 | Basf Ag | Process for the preparation of concentrated, stable water-in-oil polymer emulsions of water-soluble or water-swellable polymers |
| US4617693A (en) | 1984-08-06 | 1986-10-21 | Meyer Marjorie A | Drain pipe cleaning tool |
| FI75504C (en) | 1984-08-28 | 1988-07-11 | Ahlstroem Oy | Device in fluidized bed reactor. |
| US4595567A (en) | 1984-12-28 | 1986-06-17 | Uop Inc. | Cooling fluidized catalytic cracking regeneration zones with heat pipe apparatus |
| US4710357A (en) | 1984-12-28 | 1987-12-01 | Uop Inc. | FCC combustion zone catalyst cooling apparatus |
| US4615870A (en) | 1985-03-11 | 1986-10-07 | The M. W. Kellogg Company | Back-mixed hydrotreating reactor |
| US4584947A (en) | 1985-07-01 | 1986-04-29 | Chittick Donald E | Fuel gas-producing pyrolysis reactors |
| US4828581A (en) | 1985-09-20 | 1989-05-09 | Battelle Development Corporation | Low inlet gas velocity high throughput biomass gasifier |
| US4732091A (en) | 1985-09-30 | 1988-03-22 | G.G.C., Inc. | Pyrolysis and combustion process and system |
| US4678860A (en) | 1985-10-04 | 1987-07-07 | Arizona Board Of Regents | Process of producing liquid hydrocarbon fuels from biomass |
| US4668243A (en) | 1985-10-23 | 1987-05-26 | Schulz Johann G | Novel fuel |
| US4823712A (en) | 1985-12-18 | 1989-04-25 | Wormser Engineering, Inc. | Multifuel bubbling bed fluidized bed combustor system |
| US4891459A (en) | 1986-01-17 | 1990-01-02 | Georgia Tech Research Corporation | Oil production by entrained pyrolysis of biomass and processing of oil and char |
| SE460146B (en) | 1986-08-14 | 1989-09-11 | Goetaverken Energy Syst Ab | APPLICATION FOR COMBUSTION PLANT WITH CIRCULATING FLUID BED |
| US4849091A (en) | 1986-09-17 | 1989-07-18 | Uop | Partial CO combustion with staged regeneration of catalyst |
| US4714109A (en) | 1986-10-03 | 1987-12-22 | Utah Tsao | Gas cooling with heat recovery |
| EP0282000B1 (en) | 1987-03-11 | 1993-06-09 | Kansai Paint Co., Ltd. | Cationically electrodepositable finely divided gelled polymer and cationically electrodepositable coating composition containing same |
| US4968325A (en) | 1987-08-24 | 1990-11-06 | Centre Quebecois De Valorisation De La Biomasse | Fluidized bed gasifier |
| US4983278A (en) | 1987-11-03 | 1991-01-08 | Western Research Institute & Ilr Services Inc. | Pyrolysis methods with product oil recycling |
| US4876108A (en) | 1987-11-12 | 1989-10-24 | Ensyn Engineering Associates Inc. | Method of using fast pyrolysis liquids as liquid smoke |
| US5236688A (en) | 1987-11-13 | 1993-08-17 | Kureha Kagaku Kogyo Kabushiki Kaisha | Method for activating infusibilized pitch beads |
| US4881592A (en) | 1988-02-01 | 1989-11-21 | Uop | Heat exchanger with backmix and flow through particle cooling |
| US4992605A (en) | 1988-02-16 | 1991-02-12 | Craig Wayne K | Production of hydrocarbons with a relatively high cetane rating |
| US4942269A (en) | 1988-03-17 | 1990-07-17 | Midwest Research Institute | Process for fractionating fast-pyrolysis oils, and products derived therefrom |
| US4880473A (en) | 1988-04-01 | 1989-11-14 | Canadian Patents & Development Ltd. | Process for the production of fermentable sugars from biomass |
| JPH01277196A (en) | 1988-04-27 | 1989-11-07 | Daikin Ind Ltd | Fluid bed heat exchanger |
| US4940007A (en) | 1988-08-16 | 1990-07-10 | A. Ahlstrom Corporation | Fast fluidized bed reactor |
| US5009770A (en) | 1988-08-31 | 1991-04-23 | Amoco Corporation | Simultaneous upgrading and dedusting of liquid hydrocarbon feedstocks |
| US5059404A (en) | 1989-02-14 | 1991-10-22 | Manufacturing And Technology Conversion International, Inc. | Indirectly heated thermochemical reactor apparatus and processes |
| US5879650A (en) | 1989-04-06 | 1999-03-09 | Cabot Corporation | Tandem quench |
| US5041209A (en) | 1989-07-12 | 1991-08-20 | Western Research Institute | Process for removing heavy metal compounds from heavy crude oil |
| US4988430A (en) | 1989-12-27 | 1991-01-29 | Uop | Supplying FCC lift gas directly from product vapors |
| US5961786A (en) | 1990-01-31 | 1999-10-05 | Ensyn Technologies Inc. | Apparatus for a circulating bed transport fast pyrolysis reactor system |
| CA2009021C (en) | 1990-01-31 | 2001-09-11 | Barry A. Freel | Method and apparatus for a circulating bed transport fast pyrolysis reactor system |
| US5792340A (en) | 1990-01-31 | 1998-08-11 | Ensyn Technologies, Inc. | Method and apparatus for a circulating bed transport fast pyrolysis reactor system |
| US5225044A (en) | 1990-03-14 | 1993-07-06 | Wayne Technology, Inc. | Pyrolytic conversion system |
| US5077252A (en) | 1990-07-17 | 1991-12-31 | Mobil Oil Corporation | Process for control of multistage catalyst regeneration with partial co combustion |
| US5011592A (en) | 1990-07-17 | 1991-04-30 | Mobil Oil Corporation | Process for control of multistage catalyst regeneration with full then partial CO combustion |
| US5136117A (en) | 1990-08-23 | 1992-08-04 | Battelle Memorial Institute | Monomeric recovery from polymeric materials |
| US5018458A (en) | 1990-09-12 | 1991-05-28 | Zimpro Passavant Environmental Systems, Inc. | Furnace combustion zone temperature control method |
| US5380916A (en) * | 1990-11-02 | 1995-01-10 | University Of Florida | Method for the isolation and purification of taxane derivatives |
| JP3222466B2 (en) | 1991-04-19 | 2001-10-29 | ザ・ユニバーシティ・オブ・ミシシッピー | Methods and compositions for isolating taxanes |
| US5536488A (en) | 1991-07-01 | 1996-07-16 | Manufacturing And Technology Conversion | Indirectly heated thermochemical reactor processes |
| FR2683743B1 (en) | 1991-11-14 | 1994-02-11 | Institut Francais Petrole | METHOD AND DEVICE FOR THERMAL EXCHANGE OF SOLID PARTICLES FOR DOUBLE REGENERATION IN CATALYTIC CRACKING. |
| US5212129A (en) | 1991-12-17 | 1993-05-18 | Uop | Inverted backmix coolers for FCC units |
| IT1258838B (en) * | 1992-01-31 | 1996-02-29 | Indena Spa | PROCESS FOR THE EXTRACTION OF TASSOLO AND DERIVATIVES FROM CULTIVARS OF THE KIND TAXUS |
| SE470213B (en) | 1992-03-30 | 1993-12-06 | Nonox Eng Ab | Methods and apparatus for producing fuels from solid carbonaceous natural fuels |
| US5239946A (en) | 1992-06-08 | 1993-08-31 | Foster Wheeler Energy Corporation | Fluidized bed reactor system and method having a heat exchanger |
| JPH06184560A (en) | 1992-07-10 | 1994-07-05 | Hiroshi Shimizu | Apparatus for thermal cracking of organic waste |
| US5243922A (en) | 1992-07-31 | 1993-09-14 | Institute Of Gas Technology | Advanced staged combustion system for power generation from coal |
| US5371212A (en) | 1992-09-04 | 1994-12-06 | Midwest Research Institute | Isolation of levoglucosan from pyrolysis oil derived from cellulose |
| GB9224783D0 (en) | 1992-11-26 | 1993-01-13 | Univ Waterloo | An improved process for the thermal conversion of biomass to liquids |
| US5281727A (en) * | 1992-11-27 | 1994-01-25 | Napro Biotherapeutics, Inc. | Method of using ion exchange media to increase taxane yields |
| CA2126698A1 (en) * | 1992-12-07 | 1994-06-23 | Muraleedharan G. Nair | Process for the isolation and purification of taxol and taxanes from taxus spp. |
| US5343939A (en) | 1992-12-14 | 1994-09-06 | Uop | Offset FCC coolers with improved catalyst circulation |
| NO176455B1 (en) | 1992-12-28 | 1995-04-24 | Energos As | grate furnace |
| US5426807A (en) | 1993-02-16 | 1995-06-27 | Goodway Tools Corporation | Tube cleaning apparatus |
| US5402548A (en) | 1993-03-31 | 1995-04-04 | Adair; Michael A. | Duct cleaning apparatus |
| US5376340A (en) | 1993-04-15 | 1994-12-27 | Abb Air Preheater, Inc. | Regenerative thermal oxidizer |
| US5423891A (en) | 1993-05-06 | 1995-06-13 | Taylor; Robert A. | Method for direct gasification of solid waste materials |
| IT1261667B (en) * | 1993-05-20 | 1996-05-29 | TAX FOR ANTI-CANCER ACTIVITIES. | |
| US5494653A (en) | 1993-08-27 | 1996-02-27 | Battelle Memorial Institute | Method for hot gas conditioning |
| US5713977A (en) | 1994-09-12 | 1998-02-03 | Praxair Technology, Inc. | Fixed bed filtering preheater process for high temperature process furnaces |
| GB9426066D0 (en) | 1994-12-22 | 1995-02-22 | Radlein Desmond S G | Method of upgrading biomass pyrolysis liquids for use as fuels and as a source of chemicals by reaction with alcohols |
| US5584985A (en) | 1994-12-27 | 1996-12-17 | Uop | FCC separation method and apparatus with improved stripping |
| CH690790A5 (en) | 1995-01-10 | 2001-01-15 | Von Roll Umwelttechnik Ag | A process for the thermal treatment of waste material. |
| US5520722A (en) | 1995-01-18 | 1996-05-28 | Exxon Research And Engineering Company | Multiunsaturates removal process |
| US6398921B1 (en) | 1995-03-15 | 2002-06-04 | Microgas Corporation | Process and system for wastewater solids gasification and vitrification |
| US5662050A (en) | 1995-05-05 | 1997-09-02 | Angelo, Ii; James F. | Process for chemical/thermal treatment without toxic emissions |
| DE19524176C1 (en) | 1995-07-03 | 1996-09-26 | Daimler Benz Ag | Heat treatment process for light alloy castings |
| US5654448A (en) * | 1995-10-02 | 1997-08-05 | Xechem International, Inc. | Isolation and purification of paclitaxel from organic matter containing paclitaxel, cephalomannine and other related taxanes |
| IT1276116B1 (en) | 1995-11-10 | 1997-10-24 | O E T Calusco S R L | PROCEDURE AND PLANT FOR THE PRODUCTION OF VEGETABLE COAL BY PYROLYSIS OF WOOD PRODUCTS OR VEGETABLE BIOMASS IN GENERAL |
| FR2744037B1 (en) | 1996-01-31 | 1998-02-27 | Gec Alsthom Stein Ind | EXTERNAL FLUIDIZED BED FOR FITTING A CIRCULATING FLUIDIZED BED FIREPLACE |
| US6190542B1 (en) | 1996-02-23 | 2001-02-20 | Hydrocarbon Technologies, Inc. | Catalytic multi-stage process for hydroconversion and refining hydrocarbon feeds |
| DE69736263T2 (en) | 1996-02-27 | 2007-07-12 | Mitsubishi Heavy Industries, Ltd. | METHOD AND APPARATUS FOR RECOVERING OIL FROM PLASTIC WASTE |
| US6133499A (en) | 1996-02-29 | 2000-10-17 | Mitsubishi Heavy Industries, Ltd. | Method and apparatus for producing superheated steam using heat from the incineration of waste material |
| US5879642A (en) | 1996-04-24 | 1999-03-09 | Chevron U.S.A. Inc. | Fixed bed reactor assembly having a guard catalyst bed |
| AU725988C (en) | 1996-05-20 | 2007-11-15 | Dynamotive Energy Systems Corporation | Energy efficient liquefaction of biomaterials by thermolysis |
| US5728271A (en) | 1996-05-20 | 1998-03-17 | Rti Resource Transforms International Ltd. | Energy efficient liquefaction of biomaterials by thermolysis |
| US5703299A (en) | 1996-06-21 | 1997-12-30 | Corona Energy Partners, Ltd. | Exhaust stack sensor probe |
| US6113862A (en) | 1997-04-23 | 2000-09-05 | Union Carbide Chemicals & Plastics Technology Corporation | Fluidized bed polymerization reactor with multiple fluidization grids |
| WO1998050430A2 (en) * | 1997-05-02 | 1998-11-12 | Somatogen, Inc. | Hemoglobin mutants with increased soluble expression and/or reduced nitric oxide scavenging |
| US6033555A (en) | 1997-06-10 | 2000-03-07 | Exxon Chemical Patents Inc. | Sequential catalytic and thermal cracking for enhanced ethylene yield |
| US5879079A (en) | 1997-08-20 | 1999-03-09 | The United States Of America As Represented By The Administrator, Of The National Aeronautics And Space Administration | Automated propellant blending |
| US6193837B1 (en) | 1997-09-19 | 2001-02-27 | Midwest Research Institute | Preparation of brightness stabilization agent for lignin containing pulp from biomass pyrolysis oils |
| DE69816326T2 (en) | 1997-10-16 | 2004-04-22 | Toyota Jidosha K.K., Toyota | CATALYTIC COMBUSTION HEATER |
| JPH11148625A (en) | 1997-11-20 | 1999-06-02 | Hitachi Ltd | Device and method of recovering combustion heat of waste |
| FI104561B (en) | 1998-02-27 | 2000-02-29 | Fortum Oil And Gas Oy Fortum O | Process for pyrolysis of carbonaceous feedstock |
| US5904838A (en) | 1998-04-17 | 1999-05-18 | Uop Llc | Process for the simultaneous conversion of waste lubricating oil and pyrolysis oil derived from organic waste to produce a synthetic crude oil |
| UA45442C2 (en) | 1998-09-11 | 2002-04-15 | Емануїл Вольфович Прилуцький | CATALYST OF LOW TEMPERATURE PYROLYSIS OF POLYMERIC MATERIALS CONTAINING HYDROCARBONS |
| FI110205B (en) | 1998-10-02 | 2002-12-13 | Foster Wheeler Energia Oy | Method and apparatus in a fluidized bed heat exchanger |
| FI117512B (en) | 1998-10-14 | 2006-11-15 | Valtion Teknillinen | Method and apparatus for producing pyrolysis oil |
| FI116902B (en) | 1998-10-14 | 2006-03-31 | Valtion Teknillinen | Method and apparatus for improving the quality of the pyrolysis liquid |
| US6485841B1 (en) | 1998-10-30 | 2002-11-26 | Ensyn Technologies, Inc. | Bio-oil preservatives |
| US6106702A (en) | 1998-12-29 | 2000-08-22 | Uop Llc | Olefinic hydrocarbon separation process |
| US5969165A (en) * | 1999-01-07 | 1999-10-19 | 508037 (Nb) Inc. | Isolation and purification of paclitaxel and other related taxanes by industrial preparative low pressure chromatography on a polymeric resin column |
| WO2000061705A1 (en) | 1999-04-07 | 2000-10-19 | Ensyn Group Inc. | Rapid thermal processing of heavy hydrocarbon feedstocks |
| US6808390B1 (en) | 1999-05-04 | 2004-10-26 | Commonwealth Scientific And Industrial Research Organization | Process for carbonizing wood residues and producing activated carbon |
| US6875341B1 (en) | 1999-05-24 | 2005-04-05 | James W. Bunger And Associates, Inc. | Process for enhancing the value of hydrocabonaceous natural recources |
| CA2299149C (en) | 1999-06-22 | 2010-09-21 | Chaichem Pharmaceuticals International | Process for isolating and purifying paclitaxel from natural sources |
| DE19930071C2 (en) | 1999-06-30 | 2001-09-27 | Wolfgang Krumm | Method and device for pyrolysis and gasification of organic substances and mixtures |
| US6530964B2 (en) | 1999-07-07 | 2003-03-11 | The Lubrizol Corporation | Continuous process for making an aqueous hydrocarbon fuel |
| JP2001083645A (en) | 1999-07-13 | 2001-03-30 | Fuji Photo Film Co Ltd | Silver halide photographic sensitive material |
| US7047894B2 (en) | 1999-11-02 | 2006-05-23 | Consolidated Engineering Company, Inc. | Method and apparatus for combustion of residual carbon in fly ash |
| JP2001131560A (en) | 1999-11-09 | 2001-05-15 | Hitachi Ltd | Method and apparatus for thermally decomposing hydrocarbon raw material |
| CA2391146C (en) | 1999-11-11 | 2012-05-22 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Flash-pyrolysis in a cyclone |
| US6455015B1 (en) | 2000-02-16 | 2002-09-24 | Uop Llc | Fluid-solid contacting chambers having multi-conduit, multi-nozzle fluid distribution |
| US6452024B1 (en) * | 2000-02-22 | 2002-09-17 | Chaichem Pharmaceuticals International | Process for extraction and purification of paclitaxel from natural sources |
| US6237541B1 (en) | 2000-04-19 | 2001-05-29 | Kvaerner Pulping Oy | Process chamber in connection with a circulating fluidized bed reactor |
| AU2001252116A1 (en) | 2000-05-01 | 2001-11-12 | Danmarks Tekniske Universitet | A method and an installation for thermal gasification of solid fuel |
| US6339182B1 (en) | 2000-06-20 | 2002-01-15 | Chevron U.S.A. Inc. | Separation of olefins from paraffins using ionic liquid solutions |
| US6776607B2 (en) | 2000-06-26 | 2004-08-17 | Exxonmobil Research And Engineering Company | Process for minimizing afterburn in a FCC regenerator |
| US6676828B1 (en) | 2000-07-26 | 2004-01-13 | Intevep, S.A. | Process scheme for sequentially treating diesel and vacuum gas oil |
| EP1184443A1 (en) | 2000-09-04 | 2002-03-06 | Biofuel B.V. | Process for the production of liquid fuels from biomass |
| EP2275513A3 (en) | 2000-09-18 | 2011-04-13 | Ensyn Petroleum International Ltd. | Products produced from rapid thermal processing of heavy hydrocarbon feedstocks |
| US6547957B1 (en) | 2000-10-17 | 2003-04-15 | Texaco, Inc. | Process for upgrading a hydrocarbon oil |
| CN1098337C (en) | 2000-11-02 | 2003-01-08 | 中国石油天然气股份有限公司 | Novel normal-pressure heavy oil suspension bed hydrogenation process adopting multi-metal liquid catalyst |
| US6680137B2 (en) | 2000-11-17 | 2004-01-20 | Future Energy Resources Corporation | Integrated biomass gasification and fuel cell system |
| AUPR221700A0 (en) | 2000-12-20 | 2001-01-25 | Gosfern Pty Limited | Crude oil conditioning apparatus and method |
| CN1240810C (en) | 2001-03-30 | 2006-02-08 | 中国科学院化工冶金研究所 | Four coproduction process and equipment for circular fluiding carbon-hydrogen solid fuel |
| US6656342B2 (en) | 2001-04-04 | 2003-12-02 | Chevron U.S.A. Inc. | Graded catalyst bed for split-feed hydrocracking/hydrotreating |
| US7241323B2 (en) | 2001-07-10 | 2007-07-10 | Advanced Fuel Research, Inc. | Pyrolysis process for producing fuel gas |
| ES2235087T3 (en) | 2001-08-10 | 2005-07-01 | Shell Internationale Research Maatschappij B.V. | PROCESS TO RECOVER HOT GAS ENERGY. |
| US6830730B2 (en) | 2001-09-11 | 2004-12-14 | Spectrolanalytical Instruments | Method and apparatus for the on-stream analysis of total sulfur and/or nitrogen in petroleum products |
| US6768036B2 (en) | 2001-12-31 | 2004-07-27 | Exxonmobil Chemical Patents Inc. | Method for adding heat to a reactor system used to convert oxygenates to olefins |
| US7244399B2 (en) | 2002-04-26 | 2007-07-17 | Foster Wheeler Energia Oy | Grid construction for a fluidized bed reactor |
| US7648544B2 (en) | 2002-07-19 | 2010-01-19 | Shell Oil Company | Swirl tube separator |
| US6759562B2 (en) | 2002-07-24 | 2004-07-06 | Abb Lummus Global Inc. | Olefin plant recovery system employing a combination of catalytic distillation and fixed bed catalytic steps |
| US6960325B2 (en) | 2002-08-22 | 2005-11-01 | Hydrocarbon Technologies | Apparatus for hydrocracking and/or hydrogenating fossil fuels |
| US7026262B1 (en) | 2002-09-17 | 2006-04-11 | Uop Llc | Apparatus and process for regenerating catalyst |
| US7572365B2 (en) | 2002-10-11 | 2009-08-11 | Ivanhoe Energy, Inc. | Modified thermal processing of heavy hydrocarbon feedstocks |
| US7572362B2 (en) | 2002-10-11 | 2009-08-11 | Ivanhoe Energy, Inc. | Modified thermal processing of heavy hydrocarbon feedstocks |
| US7263934B2 (en) | 2003-02-24 | 2007-09-04 | Harris Contracting Company | Methods for generating energy using agricultural biofuel |
| FR2851570B1 (en) | 2003-02-24 | 2007-07-27 | Inst Francais Du Petrole | INSTALLATION AND METHOD FOR MULTI-STAGE GASIFICATION OF A LOAD COMPRISING ORGANIC MATTER |
| US7022741B2 (en) | 2003-03-28 | 2006-04-04 | Conocophillips Company | Gas agitated multiphase catalytic reactor with reduced backmixing |
| FI114115B (en) | 2003-04-15 | 2004-08-13 | Foster Wheeler Energia Oy | Fluidized bed reactor includes vertical auxiliary channel having lower part with nozzles and flow conduit to connect channel to furnace, and upper part with flow conduit to connect channel to heat exchange chamber |
| JP4050184B2 (en) | 2003-05-13 | 2008-02-20 | 株式会社日本触媒 | Process for producing aliphatic carboxylic acid |
| US7247233B1 (en) | 2003-06-13 | 2007-07-24 | Uop Llc | Apparatus and process for minimizing catalyst residence time in a reactor vessel |
| FI20031113A (en) | 2003-07-29 | 2005-01-30 | Outokumpu Oy | A method and apparatus for cooling material to be removed from a grate in a fluidized bed furnace |
| US7004999B2 (en) | 2003-08-18 | 2006-02-28 | Dynamotive Energy Systems Corporation | Apparatus for separating fouling contaminants from non-condensable gases at the end of a pyrolysis/thermolysis of biomass process |
| TW200519073A (en) | 2003-08-21 | 2005-06-16 | Pearson Technologies Inc | Process and apparatus for the production of useful products from carbonaceous feedstock |
| EP1668293A2 (en) | 2003-08-21 | 2006-06-14 | International Environmental Solutions Corporation | Chamber support for pyrolytic waste treatment system |
| US7285186B2 (en) | 2003-12-11 | 2007-10-23 | Zbigniew Tokarz | Transverse-flow catalytic reactor for conversion of waste plastic material and scrap rubber |
| US20050209328A1 (en) | 2004-03-19 | 2005-09-22 | Allgood Charles C | Alphahydroxyacids with ultra-low metal concentration |
| ES2585891T3 (en) | 2004-04-28 | 2016-10-10 | Headwaters Heavy Oil, Llc | Boiling bed hydroprocessing methods and systems |
| WO2006014486A1 (en) | 2004-07-07 | 2006-02-09 | California Institute Of Technology | Process to upgrade oil using metal oxides |
| US7024800B2 (en) | 2004-07-19 | 2006-04-11 | Earthrenew, Inc. | Process and system for drying and heat treating materials |
| US7685737B2 (en) | 2004-07-19 | 2010-03-30 | Earthrenew, Inc. | Process and system for drying and heat treating materials |
| EP1642878B1 (en) | 2004-10-01 | 2007-12-26 | Research Institute of Petroleum Industry | An integrated process and apparatus for producing liquid fuels |
| FR2879213B1 (en) | 2004-12-15 | 2007-11-09 | Inst Francais Du Petrole | CONNECTION OF HYDROCONVERSION AND STEAM REFORMING PROCESSES TO OPTIMIZE HYDROGEN PRODUCTION ON PRODUCTION FIELDS |
| US7473349B2 (en) | 2004-12-30 | 2009-01-06 | Bp Corporation North America Inc. | Process for removal of sulfur from components for blending of transportation fuels |
| US7829030B2 (en) | 2004-12-30 | 2010-11-09 | Exxonmobil Chemical Patents Inc. | Fluidizing a population of catalyst particles having a low catalyst fines content |
| NL1027932C2 (en) | 2004-12-31 | 2006-07-03 | Btg Biomass Technology Group B | Dipleg, method for its use and applications of the dipleg. |
| US20060163053A1 (en) | 2005-01-21 | 2006-07-27 | Bengt-Sture Ershag | Batch pyrolysis system |
| US7476774B2 (en) | 2005-02-28 | 2009-01-13 | Exxonmobil Research And Engineering Company | Liquid phase aromatics alkylation process |
| US7964761B2 (en) | 2005-05-02 | 2011-06-21 | University Of Utah Research Foundation | Processes for catalytic conversion of lignin to liquid bio-fuels and novel bio-fuels |
| DK1879979T3 (en) | 2005-05-03 | 2018-02-05 | Univ Danmarks Tekniske | Pyrolysis method and apparatus |
| US20060264684A1 (en) | 2005-05-19 | 2006-11-23 | Petri John A | Production of diesel fuel from biorenewable feedstocks |
| US7868214B2 (en) | 2005-05-19 | 2011-01-11 | Uop Llc | Production of olefins from biorenewable feedstocks |
| WO2007093225A1 (en) | 2005-05-23 | 2007-08-23 | Shell Internationale Research Maatschappij B.V. | Process for the removal of contaminants |
| US7491317B2 (en) | 2005-06-07 | 2009-02-17 | China Petroleum & Chemical Corporation | Desulfurization in turbulent fluid bed reactor |
| CN101198418B (en) | 2005-06-08 | 2010-10-20 | 西安大略大学 | Apparatus and process for the pyrolysis of agricultural biomass |
| US7727383B2 (en) | 2005-06-30 | 2010-06-01 | Amt International, Inc. | Process for producing petroleum oils with ultra-low nitrogen content |
| CN100360248C (en) | 2005-08-10 | 2008-01-09 | 重庆大学 | Biomass pyrolysis liquefied technique and double tower apparatus system thereof |
| DE102005037917A1 (en) | 2005-08-11 | 2007-02-15 | Forschungszentrum Karlsruhe Gmbh | Process for the rapid pyrolysis of lignocellulose |
| US20070051238A1 (en) | 2005-09-07 | 2007-03-08 | Ravi Jain | Process for gas purification |
| DE102005049375A1 (en) | 2005-10-15 | 2007-04-26 | Forschungszentrum Karlsruhe Gmbh | Process for the preparation and preparation of quick pyrolysis products from biomass for a flow stream pressure gasification |
| WO2007045093A1 (en) * | 2005-10-21 | 2007-04-26 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Natural Resources Canada, Canadian Forest Service | Preparation of taxanes |
| US20090217573A1 (en) | 2005-10-26 | 2009-09-03 | Kiram Ab | Automotive fuels and fine chemicals from crude tall oil |
| US7867538B2 (en) | 2005-12-20 | 2011-01-11 | Archer Daniels Midland Company | Processes of improving the quality of oil and products produced therefrom |
| JP2007229548A (en) | 2006-02-27 | 2007-09-13 | Nippon Steel Engineering Co Ltd | Reforming catalyst acted in biomass pyrolysis gasification process, its manufacturing method and modification process using the reforming catalyst, biomass pyrolytic gasifying device, and method for regenerating catalyst |
| US20070205139A1 (en) | 2006-03-01 | 2007-09-06 | Sathit Kulprathipanja | Fcc dual elevation riser feed distributors for gasoline and light olefin modes of operation |
| CA2647564C (en) | 2006-04-03 | 2016-08-30 | Pharmatherm Chemicals Inc. | Thermal extraction method and product |
| EP1852493A1 (en) | 2006-05-05 | 2007-11-07 | BIOeCON International Holding N.V. | Hydrothermal treatment of carbon-based energy carrier material |
| BRPI0711564A2 (en) | 2006-05-05 | 2011-11-08 | Bioecon Int Holding Nv | process for converting a highly viscous or solid carbon based energy carrier material into gaseous and liquid reaction products |
| US20070272538A1 (en) | 2006-05-26 | 2007-11-29 | Satchell Donald P | Flash pyrolosis method for carbonaceous materials |
| US20080006519A1 (en) | 2006-07-06 | 2008-01-10 | Badger Phillip C | Method and system for accomplishing flash or fast pyrolysis with carbonaceous materials |
| US20080006520A1 (en) | 2006-07-06 | 2008-01-10 | Badger Phillip C | Method and system for accomplishing flash or fast pyrolysis with carbonaceous materials |
| US20100209965A1 (en) | 2006-07-17 | 2010-08-19 | Bioecon International Holding N.V. | Catalytic pyrolysis of fine particulate biomass, and method for reducing the particle size of solid biomass particles |
| US20080029437A1 (en) | 2006-08-02 | 2008-02-07 | Exxonmobil Research And Engineering Company | Olefin upgrading process with guard bed regeneration |
| US7758817B2 (en) | 2006-08-09 | 2010-07-20 | Uop Llc | Device for contacting high contaminated feedstocks with catalyst in an FCC unit |
| GB0616298D0 (en) | 2006-08-16 | 2006-09-27 | Univ Aston | Biomass pyrolysis |
| EP1892280A1 (en) | 2006-08-16 | 2008-02-27 | BIOeCON International Holding N.V. | Fluid catalytic cracking of oxygenated compounds |
| WO2008020551A1 (en) | 2006-08-18 | 2008-02-21 | Nippon Oil Corporation | Method of treating biomass, fuel for fuel cell, gasoline, diesel fuel, liquefied petroleum gas, and synthetic resin |
| US20080051619A1 (en) | 2006-08-25 | 2008-02-28 | Santi Kulprathipanja | Olefin-Separation Process |
| US7578927B2 (en) | 2006-08-31 | 2009-08-25 | Uop Llc | Gasoline and diesel production from pyrolytic lignin produced from pyrolysis of cellulosic waste |
| US20080081006A1 (en) | 2006-09-29 | 2008-04-03 | Myers Daniel N | Advanced elevated feed distribution system for very large diameter RCC reactor risers |
| US7687261B2 (en) | 2006-10-13 | 2010-03-30 | General Atomics | Photosynthetic oil production in a two-stage reactor |
| US7998455B2 (en) | 2006-11-16 | 2011-08-16 | Archer Daniels Midland Company | Process for hydrogen gas production from carbohydrate feedstocks |
| FR2910483B1 (en) | 2006-12-21 | 2010-07-30 | Inst Francais Du Petrole | METHOD OF CONVERTING CHARGES FROM RENEWABLE SOURCES IN GOODLY GASOLINE FUEL BASES. |
| US20080171649A1 (en) | 2007-01-12 | 2008-07-17 | Deng-Yang Jan | Modified Y-85 and LZ-210 Zeolites |
| DE102007005835A1 (en) | 2007-02-01 | 2008-08-14 | Forschungszentrum Karlsruhe Gmbh | Method and device for converting biomass into fuel |
| US7959765B2 (en) | 2007-02-06 | 2011-06-14 | North Carolina State Universtiy | Product preparation and recovery from thermolysis of lignocellulosics in ionic liquids |
| US7737314B2 (en) | 2007-02-12 | 2010-06-15 | Exxonmobil Chemical Patents Inc. | Production of high purity ethylbenzene from non-extracted feed and non-extracted reformate useful therein |
| ES2303792B1 (en) | 2007-02-15 | 2009-06-12 | Industrias Mecanicas Alcudia S.A. | A PROCEDURE FOR THE ENERGETIC REVALUATION OF THE ORGANIC FRACTION OF URBAN SOLID WASTE, AND INSTALLATION. |
| GB2446820B (en) | 2007-02-23 | 2011-09-21 | Mark Collins | A Method of Generating Heat |
| CA2624746C (en) | 2007-03-12 | 2015-02-24 | Robert Graham | Methods and systems for producing reduced resid and bottomless products from heavy hydrocarbon feedstocks |
| GB2447684B (en) | 2007-03-21 | 2011-11-23 | Statoil Asa | Biogasoline |
| US20080282606A1 (en) | 2007-04-16 | 2008-11-20 | Plaza John P | System and process for producing biodiesel |
| CN101045524B (en) | 2007-05-04 | 2010-05-19 | 大连理工大学 | Method for preparing hydrogen-riched gas by solid fuel catalytic gasification |
| US20080272030A1 (en) | 2007-05-04 | 2008-11-06 | Boykin Jack W | Method for the production of synthetic fuels |
| US8153850B2 (en) | 2007-05-11 | 2012-04-10 | The Texas A&M University System | Integrated biofuel production system |
| US7914667B2 (en) | 2007-06-04 | 2011-03-29 | Exxonmobil Chemical Patents Inc. | Pyrolysis reactor conversion of hydrocarbon feedstocks into higher value hydrocarbons |
| US7425657B1 (en) | 2007-06-06 | 2008-09-16 | Battelle Memorial Institute | Palladium catalyzed hydrogenation of bio-oils and organic compounds |
| US8158842B2 (en) | 2007-06-15 | 2012-04-17 | Uop Llc | Production of chemicals from pyrolysis oil |
| WO2009002878A1 (en) | 2007-06-22 | 2008-12-31 | Biofuelbox Corporation | System for production and purification of biofuel |
| DE102007031461A1 (en) | 2007-07-05 | 2009-01-08 | Sappok, Manfred, Dipl.-Phys. Dr. | Process for stabilizing heating oil or diesel oil, in particular from the depolymerization of hydrocarbon-containing residues |
| CN101353582B (en) | 2007-07-25 | 2010-12-01 | 中国科学院工程热物理研究所 | Solid heat carrier rapid pyrolysis method and apparatus |
| US8105399B2 (en) | 2007-07-31 | 2012-01-31 | Endicott Biofuels Ii, Llc | Production of renewable diesel by pyrolysis and esterification |
| US8202332B2 (en) | 2007-08-01 | 2012-06-19 | Virginia Tech Intellectual Properties | Fractional catalytic pyrolysis of biomass |
| HUP0700508A2 (en) | 2007-08-03 | 2010-12-28 | 3R Carbon Capture And Storage Pty Ltd | Appliance for carbon catena development and process for neutralisation of dangerous wastes |
| US8217210B2 (en) | 2007-08-27 | 2012-07-10 | Purdue Research Foundation | Integrated gasification—pyrolysis process |
| US8217211B2 (en) | 2007-08-27 | 2012-07-10 | Purdue Research Foundation | Process for producing liquid hydrocarbon by pyrolysis of biomass in presence of hydrogen from a carbon-free energy source |
| US8003834B2 (en) | 2007-09-20 | 2011-08-23 | Uop Llc | Integrated process for oil extraction and production of diesel fuel from biorenewable feedstocks |
| US7999142B2 (en) | 2007-09-20 | 2011-08-16 | Uop Llc | Production of diesel fuel from biorenewable feedstocks |
| US7999143B2 (en) | 2007-09-20 | 2011-08-16 | Uop Llc | Production of diesel fuel from renewable feedstocks with reduced hydrogen consumption |
| US7982075B2 (en) | 2007-09-20 | 2011-07-19 | Uop Llc | Production of diesel fuel from biorenewable feedstocks with lower hydrogen consumption |
| US7982077B2 (en) | 2007-09-20 | 2011-07-19 | Uop Llc | Production of diesel fuel from biorenewable feedstocks with selective separation of converted oxygen |
| US7982078B2 (en) | 2007-09-20 | 2011-07-19 | Uop Llc | Production of diesel fuel from biorenewable feedstocks with selective separation of converted oxygen |
| FI123180B (en) | 2007-10-11 | 2012-12-14 | Valtion Teknillinen | Plant for the preparation of a pyrolysis product |
| FI123455B (en) | 2007-10-11 | 2013-05-15 | Valtion Teknillinen | Procedure for performing pyrolysis |
| US7905990B2 (en) | 2007-11-20 | 2011-03-15 | Ensyn Renewables, Inc. | Rapid thermal conversion of biomass |
| US8241605B2 (en) | 2008-01-31 | 2012-08-14 | Battelle Memorial Institute | Methods and apparatus for catalytic hydrothermal gasification of biomass |
| US20090208402A1 (en) | 2008-02-20 | 2009-08-20 | Rossi Robert A | Process and system for producing commercial quality carbon dioxide from fine particle limestone |
| CA2753985C (en) | 2008-03-04 | 2017-12-19 | University Of Massachusetts | Catalytic pyrolysis of solid biomass and related biofuels, aromatic, and olefin compounds |
| US8039682B2 (en) | 2008-03-17 | 2011-10-18 | Uop Llc | Production of aviation fuel from renewable feedstocks |
| US8058492B2 (en) | 2008-03-17 | 2011-11-15 | Uop Llc | Controlling production of transportation fuels from renewable feedstocks |
| EP2105456A1 (en) | 2008-03-25 | 2009-09-30 | KiOR Inc. | Composition comprising solid biomass coated onto a solid catalyst |
| EP2105486A1 (en) | 2008-03-25 | 2009-09-30 | KiOR Inc. | Low total acid number bio-crude |
| FI122778B (en) | 2008-03-31 | 2012-06-29 | Metso Power Oy | Pyrolysis method in conjunction with a boiler, and pyrolysis device |
| CN101550347B (en) | 2008-04-02 | 2013-01-09 | 朱复东 | Biomass slurry atomization thermal cracking process and device |
| US8329967B2 (en) | 2008-04-06 | 2012-12-11 | Uop Llc | Production of blended fuel from renewable feedstocks |
| US20090253947A1 (en) | 2008-04-06 | 2009-10-08 | Brandvold Timothy A | Production of Blended Fuel from Renewable Feedstocks |
| US8329968B2 (en) | 2008-04-06 | 2012-12-11 | Uop Llc | Production of blended gasoline aviation and diesel fuels from renewable feedstocks |
| MY150287A (en) | 2008-04-06 | 2013-12-31 | Uop Llc | Fuel and fuel blending components from biomass derived pyrolysis oil |
| US8324438B2 (en) | 2008-04-06 | 2012-12-04 | Uop Llc | Production of blended gasoline and blended aviation fuel from renewable feedstocks |
| US7897124B2 (en) | 2008-09-18 | 2011-03-01 | Gunnerman Rudolf W | Continuous process and plant design for conversion of biogas to liquid fuel |
| CN101294085A (en) | 2008-04-07 | 2008-10-29 | 赵靖敏 | Process and apparatus for producing biomass gas |
| US9908093B2 (en) | 2008-04-09 | 2018-03-06 | Velocys, Inc. | Process for converting a carbonaceous material to methane, methanol and/or dimethyl ether using microchannel process technology |
| US8100996B2 (en) | 2008-04-09 | 2012-01-24 | Velocys, Inc. | Process for upgrading a carbonaceous material using microchannel process technology |
| US7888540B2 (en) | 2008-04-11 | 2011-02-15 | General Electric Company | Integrated system and method for producing fuel composition from biomass |
| US8097090B2 (en) | 2008-04-25 | 2012-01-17 | Ensyn Renewables Inc. | Mitigation of deposits and secondary reactions in thermal conversion processes |
| US20090293344A1 (en) | 2008-05-30 | 2009-12-03 | Baker Hughes Incorporated | Process for Removing Water and Water Soluble Contaminants From Biofuels |
| US8304592B2 (en) | 2008-06-24 | 2012-11-06 | Uop Llc | Production of paraffinic fuel from renewable feedstocks |
| US20090321311A1 (en) | 2008-06-27 | 2009-12-31 | Uop Llc | Production of diesel fuel from renewable feedstocks containing phosphorus |
| US8288599B2 (en) | 2008-06-30 | 2012-10-16 | Kior, Inc. | Co-processing solid biomass in a conventional petroleum refining process unit |
| CN101318622A (en) | 2008-07-18 | 2008-12-10 | 华东理工大学 | Biomass quick cracked oil water vapour catforming hydrogen production method |
| US8092578B2 (en) | 2008-08-25 | 2012-01-10 | Eisenmann Corporation | Method and apparatus for eliminating or reducing waste effluent from a wet electrostatic precipitator |
| CN101381611B (en) | 2008-10-15 | 2012-04-11 | 中国林业科学研究院林产化学工业研究所 | Method for modifying biomass cracked oil to modified bio-oil by quality-improving of esterification and etherification |
| US7960598B2 (en) | 2008-12-08 | 2011-06-14 | Chevron U.S.A. Inc. | Selective, integrated processing of bio-derived ester species to yield low molecular weight hydrocarbons and hydrogen for the production of biofuels |
| TW201028464A (en) | 2008-12-08 | 2010-08-01 | Grace W R & Co | Process of cracking biofeeds using high zeolite to matrix surface area catalysts |
| CN101745349B (en) | 2008-12-12 | 2013-04-17 | 李群柱 | Catalyst heat removal method and device therefor |
| US8252169B2 (en) | 2008-12-16 | 2012-08-28 | Macarthur James B | Process for upgrading coal pyrolysis oils |
| US8283506B2 (en) | 2008-12-17 | 2012-10-09 | Uop Llc | Production of fuel from renewable feedstocks using a finishing reactor |
| TWI449781B (en) | 2008-12-17 | 2014-08-21 | Lummus Technology Inc | Gasification system and process with staged slurry addition |
| US8246914B2 (en) | 2008-12-22 | 2012-08-21 | Uop Llc | Fluid catalytic cracking system |
| US20100162625A1 (en) | 2008-12-31 | 2010-07-01 | Innovative Energy Global Limited | Biomass fast pyrolysis system utilizing non-circulating riser reactor |
| CN101544901B (en) | 2009-05-05 | 2012-05-23 | 江苏大学 | Method and device for preparing biological oil by biomass cracking |
| CA2759954A1 (en) | 2009-05-22 | 2010-11-25 | Robert Bartek | Processing biomass with a hydrogen source |
| US20100325954A1 (en) | 2009-06-30 | 2010-12-30 | General Electric Company | Quench chamber assembly for a gasifier |
| CN101993712B (en) | 2009-08-17 | 2013-03-06 | 中国石油大学(北京) | Method for flexibly adjusting catalytic cracking reaction-regeneration system heat balance |
| US20110068585A1 (en) | 2009-09-24 | 2011-03-24 | Alstom Technology Ltd | Method and system for capturing and utilizing energy generated in a flue gas stream processing system |
| ITMI20091630A1 (en) | 2009-09-24 | 2011-03-24 | Mec Srl | PLANT AND PROCEDURE FOR THE PRODUCTION OF ICE CARBON DIOXIDE PELLETS |
| DE102009052282B4 (en) | 2009-11-09 | 2012-11-29 | Thyssenkrupp Uhde Gmbh | Method for compensating exhaust enthalpy losses of heat recovery coke ovens |
| WO2011055390A2 (en) | 2009-11-09 | 2011-05-12 | Rohit Joshi | Method and apparatus for processing of spent lubricating oil |
| US8314275B2 (en) | 2009-11-23 | 2012-11-20 | Uop Llc | Methods for producing biomass-derived pyrolysis oils having increased phase stability |
| EP2325281A1 (en) | 2009-11-24 | 2011-05-25 | Shell Internationale Research Maatschappij B.V. | Process for the catalytic cracking of pyrolysis oils |
| US8404909B2 (en) | 2009-12-09 | 2013-03-26 | Chevron U.S.A. Inc. | Method for capturing carbon dioxide from biomass pyrolysis process |
| US20110146140A1 (en) | 2009-12-23 | 2011-06-23 | Brandvold Timothy A | Low water biomass-derived pyrolysis oil and processes for preparing the same |
| US8524087B2 (en) | 2009-12-23 | 2013-09-03 | Uop Llc | Low metal, low water biomass-derived pyrolysis oils and methods for producing the same |
| US8864999B2 (en) | 2009-12-23 | 2014-10-21 | Uop Llc | Methods for regenerating acidic ion-exchange resins and reusing regenerants in such methods |
| US8715490B2 (en) | 2009-12-23 | 2014-05-06 | Uop Llc | Low metal biomass-derived pyrolysis oils and processes for producing the same |
| US8471081B2 (en) | 2009-12-28 | 2013-06-25 | Uop Llc | Production of diesel fuel from crude tall oil |
| US8519203B2 (en) | 2010-02-17 | 2013-08-27 | Uop Llc | Low oxygen biomass-derived pyrolysis oils and methods for producing the same |
| US8404910B2 (en) | 2010-02-17 | 2013-03-26 | Uop Llc | Low oxygen biomass-derived pyrolysis oils and methods for producing the same |
| US20110239530A1 (en) | 2010-03-30 | 2011-10-06 | Uop Llc | Use of well mixed, backmixed reactors for processing of unstable bio feedstocks |
| US8575408B2 (en) | 2010-03-30 | 2013-11-05 | Uop Llc | Use of a guard bed reactor to improve conversion of biofeedstocks to fuel |
| US8251227B2 (en) | 2010-04-16 | 2012-08-28 | Kellogg Brown & Root Llc | Methods and apparatus for separating particulates from a particulate-fluid mixture |
| US20110284359A1 (en) | 2010-05-20 | 2011-11-24 | Uop Llc | Processes for controlling afterburn in a reheater and for controlling loss of entrained solid particles in combustion product flue gas |
| EP2404983A1 (en) | 2010-07-06 | 2012-01-11 | Total Raffinage Marketing | Hydroconversion process for heavy hydrocarbonaceous feedstock |
| US8499702B2 (en) | 2010-07-15 | 2013-08-06 | Ensyn Renewables, Inc. | Char-handling processes in a pyrolysis system |
| US8057641B2 (en) | 2010-07-19 | 2011-11-15 | Kior Inc. | Method and apparatus for pyrolysis of a biomass |
| US8519205B2 (en) | 2010-07-23 | 2013-08-27 | Ensyn Renewables, Inc. | Low water biomass-derived pyrolysis oils and processes for producing the same |
| US9222044B2 (en) | 2010-07-26 | 2015-12-29 | Uop Llc | Methods for producing low oxygen biomass-derived pyrolysis oils |
| US20120023809A1 (en) | 2010-07-28 | 2012-02-02 | Uop Llc | Methods for producing phase stable, reduced acid biomass-derived pyrolysis oils |
| US8083900B2 (en) | 2010-08-09 | 2011-12-27 | Kior Inc. | Removal of water from bio-oil |
| BR112013011287A2 (en) | 2010-11-12 | 2016-11-01 | Shell Int Research | process for the preparation of a biofuel and / or biochemical from a pyrolysis oil |
| US20120137939A1 (en) | 2010-12-06 | 2012-06-07 | Uop Llc | Processes and systems for producing heat for rapid thermal processing of carbonaceous material |
| SG190965A1 (en) | 2010-12-24 | 2013-07-31 | Sapphire Energy Inc | Production of aromatics from renewable resources |
| US8829258B2 (en) | 2010-12-27 | 2014-09-09 | Phillips 66 Company | Integrated FCC biomass pyrolysis/upgrading |
| WO2012092468A1 (en) | 2010-12-30 | 2012-07-05 | Kior Inc. | Production of renewable biofuels |
| US20120167454A1 (en) | 2010-12-30 | 2012-07-05 | Uop Llc | Pretreatment of fats and oils in the production of biofuels |
| US8716522B2 (en) | 2010-12-30 | 2014-05-06 | Uop Llc | Acetic acid production from biomass pyrolysis |
| US9441887B2 (en) | 2011-02-22 | 2016-09-13 | Ensyn Renewables, Inc. | Heat removal and recovery in biomass pyrolysis |
| US8236173B2 (en) | 2011-03-10 | 2012-08-07 | Kior, Inc. | Biomass pretreatment for fast pyrolysis to liquids |
| US8100990B2 (en) | 2011-05-15 | 2012-01-24 | Avello Bioenery, Inc. | Methods for integrated fast pyrolysis processing of biomass |
| US9193924B2 (en) | 2011-06-16 | 2015-11-24 | Uop Llc | Methods and apparatuses for forming low-metal biomass-derived pyrolysis oil |
| US9475960B2 (en) | 2011-07-29 | 2016-10-25 | Inaeris Technologies, Llc | Coating composition |
| US9347005B2 (en) | 2011-09-13 | 2016-05-24 | Ensyn Renewables, Inc. | Methods and apparatuses for rapid thermal processing of carbonaceous material |
| US9109174B2 (en) | 2011-09-20 | 2015-08-18 | Phillips 66 Company | Advanced cellulosic renewable fuels |
| US9044727B2 (en) | 2011-09-22 | 2015-06-02 | Ensyn Renewables, Inc. | Apparatuses and methods for controlling heat for rapid thermal processing of carbonaceous material |
| US10041667B2 (en) | 2011-09-22 | 2018-08-07 | Ensyn Renewables, Inc. | Apparatuses for controlling heat for rapid thermal processing of carbonaceous material and methods for the same |
| US20130212930A1 (en) | 2011-09-30 | 2013-08-22 | Chevron Usa, Inc. | Process for producing a refinery stream-compatible bio-oil from a lignocellulosic feedstock |
| EP2771435A4 (en) | 2011-10-26 | 2015-11-11 | Res Usa Llc | Gasifier fluidization |
| JP2014534318A (en) | 2011-10-31 | 2014-12-18 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイＳｈｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌｅ Ｒｅｓｅａｒｃｈ Ｍａａｔｓｃｈａｐｐｉｊ Ｂｅｓｌｏｔｅｎｖｅｎｎｏｏｔｓｈａｐ | Method for upgrading oil, fuel product, and hydrocarbon product fraction |
| AU2012338868A1 (en) | 2011-11-14 | 2014-05-01 | Shell Internationale Research Maatschappij B.V. | Process for conversion of a cellulosic material |
| US9109177B2 (en) | 2011-12-12 | 2015-08-18 | Ensyn Renewables, Inc. | Systems and methods for renewable fuel |
| US9068126B2 (en) | 2011-12-14 | 2015-06-30 | Uop Llc | Methods for deoxygenating biomass-derived pyrolysis oil |
| US8940060B2 (en) | 2011-12-15 | 2015-01-27 | Uop Llc | Methods and apparatuses for forming low-metal biomass-derived pyrolysis oil |
| US8877995B2 (en) | 2011-12-16 | 2014-11-04 | Uop Llc | Pyrolysis fuels and methods for processing pyrolysis fuels |
| US9242219B2 (en) | 2012-01-30 | 2016-01-26 | PHG Energy, LLC | Fluidized bed biogasifier and method for gasifying biosolids |
| US8546635B1 (en) | 2012-04-04 | 2013-10-01 | Uop Llc | Methods and apparatuses for preparing upgraded pyrolysis oil |
| US9670413B2 (en) | 2012-06-28 | 2017-06-06 | Ensyn Renewables, Inc. | Methods and apparatuses for thermally converting biomass |
| MY174963A (en) | 2012-08-24 | 2020-05-29 | Ensyn Renewables Inc | Devolatilization of thermally produced liquids |
| US9150466B2 (en) | 2012-11-20 | 2015-10-06 | Uop Llc | Counter-current fluidized bed reactor for the dehydrogenation of olefins |
| US9023285B2 (en) | 2012-11-20 | 2015-05-05 | Uop Llc | Counter-current fluidized bed reactor for the dehydrogenation of olefins |
| EP3492559A1 (en) | 2013-06-26 | 2019-06-05 | Ensyn Renewables, Inc. | Methods for renewable fuel |
-
2007
- 2007-04-02 CA CA2647564A patent/CA2647564C/en active Active
- 2007-04-02 WO PCT/CA2007/000535 patent/WO2007112570A1/en active Application Filing
- 2007-04-02 US US12/295,916 patent/US9127208B2/en active Active
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-
2015
- 2015-07-29 US US14/812,711 patent/US9809564B2/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1300966A (en) * | 1970-03-10 | 1972-12-29 | Yoshizo Sakamoto | Methods for processing medicinal plants and herbs |
| US5395455A (en) * | 1992-03-10 | 1995-03-07 | Energy, Mines And Resources - Canada | Process for the production of anhydrosugars from lignin and cellulose containing biomass by pyrolysis |
| US6002025A (en) * | 1999-02-24 | 1999-12-14 | Bcm Developement Inc. | Method for the purification of taxanes |
| WO2001009243A1 (en) * | 1999-07-29 | 2001-02-08 | Ensyn Group, Inc. | Novel natural resin formulations |
| US6844420B1 (en) * | 1999-07-29 | 2005-01-18 | Ensyn Renewables, Inc. | Natural resin formulations |
| CN1362959A (en) * | 2000-02-02 | 2002-08-07 | 佛罗里达州立大学研究基金有限公司 | C10 carbamoyloxy substituted taxanes as antitumor agents |
| CA2521829A1 (en) * | 2004-09-30 | 2006-03-30 | University Of Ottawa | Process for extracting taxanes |
Non-Patent Citations (3)
| Title |
|---|
| B.J. CASS，等: "Challenges in the isolation of taxanes from Taxus canadensis by fast pyrolysis", 《JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS》 * |
| CARMEN W. HUIE: "A review of modern sample-preparation techniques for the extraction and analysis of medicinal plants", 《ANAL BIOANAL CHEM》 * |
| ROGER M. SMITH: "E xtractions with superheated water", 《JOURNAL OF CHROMATOGRAPHY A》 * |
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| EP2007744A4 (en) | 2014-03-26 |
| DK2007744T3 (en) | 2017-08-28 |
| EP3252128B1 (en) | 2019-01-02 |
| US9127208B2 (en) | 2015-09-08 |
| EP3252128A3 (en) | 2018-03-28 |
| WO2007112570A1 (en) | 2007-10-11 |
| DK3252128T3 (en) | 2019-04-01 |
| CN101460473A (en) | 2009-06-17 |
| US9809564B2 (en) | 2017-11-07 |
| EP3252128A1 (en) | 2017-12-06 |
| CA2647564C (en) | 2016-08-30 |
| CA2647564A1 (en) | 2007-10-11 |
| EP2007744A1 (en) | 2008-12-31 |
| EP2007744B1 (en) | 2017-05-17 |
| CN102702139B (en) | 2016-01-20 |
| US20090298927A1 (en) | 2009-12-03 |
| US20160024037A1 (en) | 2016-01-28 |
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